O-Benzyloxime ethers and crop protection agents containing these compounds

ABSTRACT

O-Benzyloxime ethers of the formula I ##STR1## where 5 X is substituted or unsubstituted CH 2 , NOalkyl 
     Y is 
     O, S, NR 5   
     R 1 , R 2 , R 5  are H, alkyl 
     Z 1 , Z 2  are H, halogen, methyl, methoxy, cyano 
     R 3 , R 4  are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, 
     N(R 6 ) 2 , where R 6  is H, alkyl, substituted or unsubstituted phenyl, 
     --CO--N(R 7 ) 2 , where R 7  is H, substituted or unsubstituted alkyl, 
     substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclyloxy, 
     R 3  and R 4  together may form a carbocyclic or heterocyclic ring which is substituted or unsubstituted, and 
     R 3  or R 4  may be halogen, or ##STR2##  may be ##STR3## where n is an integer from 1 to 4, and 
     R 8  is, or, when n&gt;1, the R 8&#39;  s are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy, C 1  -C 4  -haloalkyl, C 1  -C 4  -haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy. 
     and crop protection agents containing these compounds.

This is a Division, of application Ser. No. 08/328,516, filed on Oct. 25, 1994, which is a Division of application Ser. No. 08/165,413, filed on Dec. 13, 1993, now U.S. Pat. No. 5,387,607, which is a Division of application Ser. No. 07/962,340, filed on Oct. 15, 1992, now U.S. Pat. No. 5,292,759, which is a Division of application Ser. No. 07/722,209, filed on Jun. 27, 1991, now U.S. Pat. No. 5,194,662.

The present invention relates to novel O-benzyloxime ethers and a method for controlling pests, in particular fungi, insects, nematodes and spider mites with these compounds.

It is known that substituted phenylacetic acid oxime derivatives can be used as fungicides (European Patent 253,213). However, their action is unsatisfactory.

We have found, surprisingly, that O-benzyloxime ethers of the general formula I ##STR4## where X is CH₂, CH--C₁ -C₄ -alkyl, CH--C₁ -C₄ -alkoxy, CH--C₁ -C₄ -alkylthio or N--C₁ -C₄ -alkoxy,

Y is O, S or NR⁵,

R¹, R² and R⁵ are each H or C₁ -C₄ -alkyl,

Z¹ and Z² are identical or different and are each H, halogen, methyl, methoxy or cyano,

R³ and R⁴ are identical or different and are each hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, C₁ -C₄ -alkylcarbonyl, unsubstituted or substituted phenylcarbonyl, unsubstituted or substituted benzylcarbonyl, C₁ -C₄ -alkoxycarbonyl, unsubstituted or substituted phenoxycarbonyl, unsubstituted or substituted benzyloxycarbonyl, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted aryl-C₁ -C₄ -alkyl, unsubstituted or substituted aryl-C₁ -C₄ -alkenyl, unsubstituted or substituted aryloxy-C₁ -C₄ -alkyl, unsubstituted or substituted arylthio-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl, unsubstituted or substituted hetaryloxy, unsubstituted or substituted hetarylthio, unsubstituted or substituted hetaryl-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl, unsubstituted or substituted hetaryl-oxy-C₁ -C₄ -alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyloxy, N(R⁶)₂, where the radicals R⁶ are identical or different and are each H, C₁ -C₆ -alkyl or unsubstituted or substituted phenyl, or

--CO--N(R⁷)₂, where the radicals R⁷ are identical or different and are each H or C₁ -C₄ -alkyl, substituents, in addition to hydrogen, being halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ - or C₂ -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, C₃ -C₆ -cycloalkyl, heterocyclyl or heterocyclyloxy, or

R³ and R⁴ together may form a carbocyclic or heterocyclic ring which may be substituted by the abovementioned substituents, and R³ or R⁴ may be halogen, or ##STR5## may be ##STR6##

where

n is an integer from 1 to 4, and

R⁸ is, or, when n>1, the R⁸ 's are identical or different and are each, H, halogen, cyano, nitro or substituted or unsubstituted

C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, aryl, aryloxy, benzyloxy, hetaryl or hetaryloxy,

have excellent fungicidal, insecticidal, nematicidal and acaricidal activity which is better than that of the known phenylacetic acid derivatives.

The fungicidal action is preferred.

The radicals stated for the general formula I may, for example, have the following meanings: X may be C₁ -C₄ -alkylidene (eg. methylidene, ethylidene, n- or isopropylidene, n-, iso-, sec- or tert-butylidene), C₁ -C₄ -alkoxymethylidene (eg. methoxy-, ethoxy-, n-propoxy, isopropoxy-, n-butoxy-, isobutoxy-, sec-butoxy- or tert-butoxymethylidene), C₁ -C₄ -alkylthiomethylidene (eg. methyl-, ethyl-, n-propyl-, isopropyl-, n-butylthio-, isobutylthio-, sec-butylthio- or tert-butylthiomethylidene) or C₁ -C₄ -alkoximino (eg. methoximino, ethoximino, n-propoximino, isopropoximino, n-butoximino, isobutoximino, sec-butoximino or tert-butoximino), Y may be O, S or NR⁵,

R¹, R² and R⁵ may each be H or C₁ -C₄ -alkyl (eg. methyl, ethyl, n- or isopropyl, n- or iso-, sec- or tert-butyl), Z¹ and Z² may be H, halogen (eg. fluorine, chlorine, bromine or iodine), methyl, methoxy or cyano, and

R³ and R⁴ may be identical or different and are each hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl (eg. methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, n-, iso-, sec-, tert- or neopentyl, n-hexyl or n-decyl), C₁ -C₄ -haloalkyl (eg. trifluoromethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, fluorodichloromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl or pentachloroethyl),

C₃ -C₆ -cycloalkyl (eg. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl),

C₃ -C₆ -halocycloalkyl (eg. 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-dichloro-3-methylcyclopropyl or tetrafluorocyclobutyl), C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl (eg. 1-methylcyclopropyl, 2,2-dimethylcyclopropyl or 1-methylcyclohexyl),

C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl (eg. methoxymethyl, ethoxymethyl, n- or isopropoxymethyl, n-, iso-, sec- or tert-butoxymethyl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, 2-n- or isopropoxyprop-2-yl or 2-n-, iso-, sec- or tert-butoxyprop-2-yl), C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl (eg. methylthiomethyl, ethylthiomethyl, n- or isopropylthiomethyl, n-, iso-, sec- or tert-butylthiomethyl, 2-methylthioprop-2-yl, 2-ethylthioprop-2-yl, 2-n- or isopropylthioprop-2-yl or 2-n-, iso-, sec- or tert-butylthioprop-2-yl),

aryl(phenyl)thio-C₁ -C₄ -alkyl (eg. phenylthiomethyl or 2-chlorophenylthiomethyl),

C₂ -C₆ -alkenyl (eg. vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 3-methyl-2-butenyl or 2-methyl-2-penten-5-yl),

C₂ -C₅ -haloalkenyl (eg. 2,2-difluorovinyl, 2,2-dichlorovinyl, 3,3,3-trifluoropropenyl, 3,3,3-trichloropropenyl or 3-chloro-2-propenyl),

C₃ -C₆ -cycloalkenyl (eg. cyclopent-1-enyl, cyclopentadienyl or cyclohex-1-enyl),

C₃ -C₆ -halocycloalkenyl (eg. pentafluorocyclopentadienyl or pentachlorocyclopentadienyl),

C₂ -C₄ -alkynyl (eg. ethynyl, 1-propynyl or 1-propargyl),

C₁ -C₄ -alkoxy (eg. methoxy, ethoxy, n- or isopropoxy or n-, iso-, sec- or tert-butoxy),

C₁ -C₄ -alkylthio (eg. methylthio, ethylthio, n- or isopropylthio or n-, iso-, sec- or tert-butylthio) or benzylthio,

C₁ -C₄ -haloalkoxy (eg. trifluoromethoxy, pentafluoroethoxy or 1,1,2,2-tetrafluoroethoxy),

N(R⁶)₂ (eg. amino, methylamino, dimethylamino, ethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino or diisobutylamino),

C₁ -C₄ -alkylcarbonyl (eg. acetyl, propionyl, butyryl, isobutyryl or pivaloyl),

unsubstituted or substituted phenylcarbonyl (eg. benzoyl or 4-chlorobenzoyl),

unsubstituted or substituted benzylcarbonyl (eg. benzylcarbonyl),

C₁ -C₄ -alkoxycarbonyl (eg. methoxycarbonyl, ethoxycarbonyl,

n- or isopropoxycarbonyl or n-, iso-, sec- or tert-butoxycarbonyl),

unsubstituted or substituted phenoxycarbonyl (eg. phenoxycarbonyl or 4-chlorophenoxycarbonyl),

unsubstituted or substituted benzyloxycarbonyl (eg. benzyloxycarbonyl),

--CO--N(R⁷)₂ (eg. aminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, diisopropylaminocarbonyl, phenylaminocarbonyl or N-methyl-N-phenylaminocarbonyl),

unsubstituted or substituted aryl (eg. phenyl, naphthyl or anthryl),

unsubstituted or substituted aryloxy (eg. phenoxy, naphthyloxy or anthryloxy),

unsubstituted or substituted arylthio (eg. phenylthio),

unsubstituted or substituted aryl-C₁ -C₄ -alkyl ( eg. benzyl, 1-phenethyl, 2-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 2-methyl-3-phenylpropyl, 2-methyl-2-phenylpropyl or 4-phenylbutyl),

unsubstituted or substituted aryl-C₁ -C₄ -alkenyl (eg. phenyl-1-ethenyl, 2-phenyl-1-propenyl, 2,2-diphenylethenyl, 1-phenyl-1-propen-2-yl or 1-phenyl-1-ethenyl), unsubstituted or substituted aryloxy-C₁ -C₄ -alkyl (eg. phenoxymethyl),

unsubstituted or substituted arylthio-C₁ -C₄ -alkyl (eg. phenylthiomethyl),

unsubstituted or substituted hetaryl (eg. pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 2,6-pyrimidinyl, 1,5-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl or 2-benzothiazolyl),

unsubstituted or substituted hetaryloxy (eg. 2-pyridyloxy or 2-pyrimidinyloxy),

unsubstituted or substituted hetarylthio (eg. 2-pyridylthio, 2-pyrimidinylthio or 2-benzothiazolylthio),

unsubstituted or substituted hetaryl-C₁ -C₄ -alkyl (eg. 2-pyridylmethyl or 3-pyridylmethyl),

unsubstituted or substituted hetaryloxy-C₁ -C₄ -alkyl (eg. furfurylmethoxy, thienylmethoxy, 3-isoxasolylmethoxy, 2-oxasolylmethoxy or 2-pyridylmethoxy),

unsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl (eg. 2'-furyl-2-ethenyl, 2'-thienyl-2-ethenyl or 3'-pyridyl-2-ethenyl),

unsubstituted or substituted heterocyclyl (eg. oxiranyl, 1-aziridinyl, 1-azetidinyl, 1-pyrrolidinyl, 2-tetrahydrofuryl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 1-piperidinyl, 1-morpholinyl, 1-piperazinyl, 1,3-dioxanyl or 3-tetrahydrothiopyranyl) or

unsubstituted or substituted heterocyclyloxy (eg. 2-dihydropyranyloxy or 2-tetrahydropyranyloxy).

The radicals referred to above in connection with unsubstituted or substituted are, in addition to hydrogen, for example, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, methoximinomethyl, ethoximinomethyl, n-propoximinomethyl, n-butoximinomethyl, n-pentyloximinomethyl, n-hexyloximinomethyl, allyloximinomethyl, benzyloximinomethyl, isopropoximinomethyl, isobutoximinomethyl, tert-butoximinomethyl, methylimino-1-ethyl, ethoximino-1-ethyl, n-propoximino-1-ethyl, n-butoximino-1-ethyl, n-pentyloximino-1-ethyl, n-hexyloximino-1-ethyl, allyloximino-1-ethyl, benzyloximino-1-ethyl, phenyl, phenoxy, benzyloxy, imidazol-1-yl, piperazin-1-yl, 4-morpholinyl, piperidin-1-yl, pyrid-2-yloxy, cyclopropyl, cyclohexyl, oxiranyl, 1,3-dioxan-2-yl, 1,3-dioxolan-2-yl and tetrahydropyran-2-yloxy.

The group ##STR7## may also be the radical of a carbocyclic or heterocyclic oxime (eg. cyclopentanone oxime, cyclohexanone oxime, cycloheptanone oxime, 2-adamantanone oxime, D-camphor oxime, 1-tetralone oxime, 1-indanone oxime, 9-fluorenone oxime, 1-methyl-4-piperidone oxime, violuric acid or N,N-dimethylvioluric acid).

R³ and R⁴ together then form, for example, a cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, camphenyl, tetralin, indane or fluorene ring.

One of the radicals R³ or R⁴ may furthermore be halogen (eg. fluorine, chlorine, bromine or iodine).

n may be 1, 2, 3 or 4 and R⁸ may be for example H, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethoxy, 1,1,2,2-tetrafluoromethoxy, phenyl, phenoxy, benzyloxy or pyrid-2-yl, where these radicals in turn may be substituted by fluorine, chlorine, bromine, iodine, cyano, methyl or methoxy.

Among the compounds in which R³ and R⁴ are hydrogen, the preferred compounds are those in which either only R³ or only R⁴ is hydrogen, in particular the compounds in which R³ is hydrogen.

Also preferred are compounds of the formula II in which x is CH₂, CHCH₃, CHC₂ H₅, CHOCH₃, CHOC₂ H₅, CHSCH₃ or CHSC₂ H₅, Y is 0, R¹ is C₁ -C₄ -alkyl, R² is H or methyl, R³ and R⁴ are identical or different and each is hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₂ -C₄ -haloalkenyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁ -C₄ -alkyl, substituted or unsubstituted aryl-C₂ -C₄ -alkenyl, substituted or unsubstituted aryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio or substituted or unsubstituted heterocyclyl, or each is N(R⁶)₂, R⁶ being identical or different and denoting M, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl or substituted or unsubstituted phenyl, or each is --CO--N(R⁷)₂, R⁷ being identical or different and denoting H or C₁ -C₄ -alkyl, the term "substituted" denoting the radicals listed in claim 1, and R³ and R⁴ may together denote a carbocyclic or heterocyclic ring which may be substituted by the radicals given under "substituted", and R³ and R⁴ may be halogen, and Z¹ and Z² are hydrogen, fluorine, chlorine, bromine, iodine, methyl, cyano or methoxy.

Owing to the C═C or C═N double bonds, the novel compounds of the general formula I may be obtained in the preparation as E/Z isomer mixtures. These can be separated into the individual components in a conventional manner, for example by crystallization or chromatography.

Both the individual isomeric compounds and mixtures thereof form subjects of the invention and can be used as pesticides.

The compounds of the general formula I as claimed in claim 1 are prepared, for example, as described in Scheme 1 (Z¹ and Z² are each H). ##STR8##

The compounds of the general formula I in which X is CH₂, CH-alkyl or CH-alkoxy can be prepared, for example, from the ketoesters 4 by a Wittig or Wittig-Horner reaction (cf. European Patents 348,766 and 178,826 and DE 3 705 389). The similar compounds 5 are likewise obtained from the ketoesters 2.

Alternatively, it is also possible to adopt a procedure in which compounds of the formula 7 or 9 are condensed with suitable reagents, for example with formaldehyde where X is CH₂ (cf. DE 3317356), a) with aldehydes (cf. D. M. Brown, J. Chem. Soc. 1948, 2147) or b) first with N,N-dimethylformamide dimethyl acetal, followed by reaction with a Grignard reagent (similarly to C. Jutz, Chem. Ber. 91 (1958), 1867) where X is CH-alkyl, or with a formate followed by alkylation (cf. European Patent 178,826) where X is CH--O-alkyl. Further preparation methods for the compounds of the formula 5 and I where X is CH--O-alkyl are described in European Patent 178,826.

Another possible method for preparing the compounds of the formula I where X is CH-alkyl and YR₂ is COOAlk is to react ketene acetals with phenylchlorocarbenes (S. N. Slougui and G. Rousseau, Synth. Commun. 12 (5) (1982), 401-407).

For compounds of the general formula I where X is CH--S-alkyl, the preparation can be carried out by the methods described in European Patents 244,077 or 310,954.

The intermediates of the formulae 3, 6 and 8 can be prepared from the compounds 2, 5 and 7 by halogenating the latter by a known method, for example with chlorine, bromine or N-bromosuccinimide, in an inert solvent (eg. CCl₄ or cyclohexane), with exposure to, for example, a Hg vapor lamp or in the presence of a free radical initiator, eg. dibenzoyl peroxide, or by introducing the radicals L, eg. mesylate, tosylate, acetate or triflate, via suitable intermediates (where L is halogen or OH).

The oxime ethers of the formula I where X is N-Oalkyl can be prepared from 4 a) by reaction with an O-alkylhydroxylamine hydrochloride or b) with hydroxylamine hydrochloride and subsequent alkylation with an alkylating agent (eg. an alkyl iodide, dialkyl sulfate, etc.) (cf. DE 3 623 921).

Furthermore, a phenylacetic ester of the formula 9 can be converted with a base (eg. NaOMe, NaH, K tertbutylate, etc.) in a solvent (eg. diethyl ether, toluene, tert-butanol, etc.) by a method similar to that in European Patent 254,426 into its anion and can be converted into the oxime with a suitable nitrosating agent (such as methyl nitrite, amyl nitrate, tert-butyl nitrite, etc.). The resulting oximate is alkylated with an alkylating agent (eg. an alkyl iodide or dialkyl sulfate).

The same processes can also be applied to the compounds of the formulae 2 and 7, and the resulting oxime ethers 5 can be converted in a known manner (European Patent 254,426) via the intermediates 6 (L is, for example, halogen) into the desired compounds I.

In the preparation processes described above, Y-R¹ is usually alkoxy.

The compounds in which YR¹ is OH (11) can be prepared by methods known from the literature (Organikum 16th edition, pages 415 and 622), from the compounds of the general formula I where YR¹ is COOAlkyl (10) (cf. Scheme 2): ##STR9##

Alternatively, the nitriles 12 can be converted in a known manner (cf. Organikum 16th edition, page 424 et seq. (1985) into the carboxylic acids 11.

The resulting carboxylic acids 11 can be converted in a conventional manner into the acyl chlorides 14 (cf. Organikum 16th edition, page 423 et seq. (1985). The conversion of 14 into the amides 15 is effected by methods similar to that described in Organikum 16th edition, page 412 (1985).

The thioesters 13 are obtained from the acyl chlorides 14 (similarly to Houben-Weyl Vol. 8, page 464 et seq. (1952)).

Alternatively, the thioesters 13 can also be prepared from the acids 11 (similarly to Houben-Weyl Vol. E5, page 855 et seq. (1985)).

The amides 15 in which R¹ and R⁵ are each H can also be prepared from the nitriles 12 by processes known from the literature (cf. Synthesis 1980, 243).

The preparation of the compounds of the general formulae 2 and 7 with ortho-methyl substitution at the aromatic (R² =H) is known.

(YR¹ =OAlkyl; cf. European Patents 178,826 and 260,832).

The oximes required for the preparation of the compounds of the general formula I are either known or can be prepared by one of the processes shown in Scheme 3. ##STR10##

Methods for the conversion of 16 or 18 into 17 are described in Houben-Weyl, Vol. 10/4 (1968).

Furthermore, aldoximes 19 can be chlorinated by known methods and can be reacted with, for example, a cyanide to give the derivatives 17 (R⁴ =CN) (cf. M. R. Zimmermann J. f. prakt. Chemie 66 (1902), 359).

The specific derivatives in which R³ is CN and R⁴ is alkoxyalkyl are prepared according to European Patent 74,047, those in which R³ is CN and R⁴ is alkylthioalkyl according to European Patent 150,822 and those in which R³ is CN and R⁴ is alkyl according to DE 2 304 848.

The method employing Me₃ SiO--NH--SiMe₃ (R. U. Hoffmann and G. A. Buntain, Synthesis 1987, 831) is used for sterically hindered ketones. ##STR11##

The novel compounds of the general formula I as claimed in claim 1 are prepared, for example, by a method in which an oxime of the formula 17 is reacted with a substituted benzyl compound 6 in which L is a leaving group (eg. chloride, bromide, p-toluenesulfonate, methanesulfonate, triflate or acetate). R¹ --R⁴, X and Y have the abovementioned meanings.

The reactions described can be carried out, for example, in an inert solvent (eg. acetone, acetonitrile, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone or pyridine) with the use of a base (eg. sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride of sodium methylate).

The reactions can also be carried out in a two-phase system (eg. dichloromethane or water) with the aid of a suitable phase transfer catalyst (eg. cetyltrimethylammonium chloride or benzyltrimethylammonium chloride).

Another method for the preparation of compounds I (YR¹ =OAlkyl, X=CH-OAlkyl or N-OAlkyl and L=Cl, Br, tosylate or mesylate) is illustrated by Scheme 5: ##STR12##

This synthesis sequence is carried out, as far as compound 22, similarly to the methods described in European Patent 244,786.

For example, N-hydroxyphthalimide can be converted with a halide or sulfonic ester 6 in the presence of an acid acceptor (eg. triethylamine, potassium carbonate, etc.), in a suitable solvent (eg. N-methylpyrrolidone, dimethylformamide, etc.), into the imidoether 21.

Cleavage to give the O-substituted hydroxylamine 22 can be effected with a mineral acid (eg. HCl; cf. Houben-Weyl Vol. 10/1, page 1181 et seq.) or with a base (for example with hydrazine or ethanolamine).

The conversion of amine 22 to I is carried out in a conventional manner (cf. D. Otzanak, J.C.S. Chem. Commun. 1986, 903).

The Examples and methods which follow are intended to illustrate the preparation of the novel active ingredients and of the novel intermediates.

Method 1: 3,4Dichloroacetophenone oxime

12.0 g (0.17 mol) of hydroxylammonium hydrochloride and 18.9 g (0.1 mol) of 3,4-dichloroacetophenone are added to a mixture of 20 ml of H₂ O, 100 ml of methanol and 8 g (0.1 mol) of pyridine. Refluxing is carried out for 1 hour, after which the mixture is acidified with 2N HCl and extracted with 3×100 ml of tert-butyl methyl ether. The organic phase is washed with water, dried with Na₂ So₄ and evaporated down. 19.6 g (96% of theory) of crystals of melting point 92° C., which according to ¹ H-NMR consist of 90% of trans-oxime, are obtained.

Method 2: 2-Oximino-2-tetrahydropyran-2'-ylacetonitrile

265.4 g (2.05 mol) of tetrahydrofuran-2-carbaldehyde oxime in 2 l of diethyl ether are initially taken at from -55° to -60° C. 153.5 g (2.15 mol) of chlorine are then passed in and the temperature is increased to -20° C.; stirring is carried out for 1 hour, the mixture is then evaporated down in a rotary evaporator at 10° C., the residue is taken up in 1.5 l of diethyl ether and the solution is stirred overnight in the absence of light, while cooling with ice. The solution is then filtered and the filtrate is added dropwise, while cooling with ice, to 147.3 g (2.27 mol) of potassium cyanide in 1 l of methanol at 10°-15° C. (exothermic). Stirring is carried out for 5 hours at room temperature (20° C.), after which the precipitate is filtered off under suction and washed twice with diethyl ether. The organic phases are partitioned between tert-butyl methyl ether and water and the residue of the ether phases is crystallized from dichloromethane/n-hexane at 0° C.

After filtration under suction and drying, 208 g (66% of theory) of a spectroscopically pure substance of melting point 105°-106° C. remain.

Method 3: 3-Methoxy-3-methyl-2-oximinobutyronitrile

53.6 g (0.46 mol) of 2-methoxy-2-methylpropionaldehyde oxime in ether (about 1M) are initially taken at from -5° to -10° C. 35.8 g (0.5 mol) of chlorine gas are passed in, after which stirring is carried out for 1 hour at this temperature and the mixture is then evaporated down at 10° C. and the residue is taken up in diethyl ether. 24.7 g (0.5 mol) of sodium cyanide in 375 ml of 20:1 methanol/H₂ O are initially taken at 10° C. and the above ethereal solution is rapidly added dropwise. After 4 hours at room temperature, the mixture is filtered under suction and the residue is washed with twice 100 ml of methanol. The combined solutions are evaporated down and the residue is partitioned between methyl tert-butyl ether and water. Drying the organic phase over Na₂ SO₄, evaporating down and crystallizing from dichloromethane/n-hexane give 41.1 g (63% of theory) of a white powder of melting point 102°-104° C.

Method 4: Methyl 3-methoxy-2-[2'-(phthalimido-oxy)-methyl]-phenylacrylate

10 g (35 mmol) of methyl 3-methoxy-2-(2'-bromomethyl)-phenylacrylate, 5.7 g (35 mmol) of hydroxyphthalimide, 3.9 g (38.6 mmol) of triethylamine and 50 ml of N-methylpyrrolidone are combined and the mixture is stirred for 2 hours at 60° C. It is then poured onto ice water, and the residue is filtered off under suction, washed with water and isopropanol and dried under reduced pressure. 9.0 g (70% of theory) of a crystalline product of melting point 156°-158° C. remain.

¹ H-NMR (CDCl₃): δ=3.60 (s, 3H); 3.75 (s, 3H); 5.12 (s, 2H); 7.13 (dbr, 1H); 7.35 (m, 2H); 7.62 (s, 1H); 7.7-7.9 (m, 5H)

Method 5: Methyl 3-methoxy-2-(2'-aminooxymethyl)-phenylacrylate

10.0 g (27 mmol) of the product from Method 4 are dissolved in 150 ml of methanol and the solution is stirred with 1.4 g (27 mmol) of hydrazine hydrate for 2 hours at room temperature. The precipitate is filtered off under suction, the mother liquor is evaporated down, the residue is stirred with diethyl ether, the precipitate is filtered off under suction again and the mother liquor is evaporated down. 6.0 g (92% of theory) of a yellow oil result (purity according to ¹ H-NMR about 90%). ¹ H-NMR (CDCl₃): δ=3.71 (s, 3H); 3.80 (s, 3H); 4.60 (s, 2H); (5.35 (sbr, 2H); 7.0-7.50 (m, 4H); 7.58 (s, 1H).

Method 6: Methyl 2-methoximino-2-(2'-phthalimidooxymethyl)-phenylacetate

2.0 g (7 mmol) of methyl 2-methoximino-2-(2'-bromomethyl)-phenylacetate, 1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7. mmol) of triethylamine are dissolved in 10 ml of N-methylpyrrolidone and the solution is stirred for 2 hours at 70° C. For working up, ice water is added, and the crystals are filtered off under suction, washed with water and methyl tert-butyl ether and dried.

1.5 g (58% of theory) of crystals of melting point 152°-155° C. remain.

¹ N-NMR (CDCl₃): δ=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr, 1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H)

Method 7: Methyl 2-methoximino-2-(2'-aminooxymethyl)-phenylacetate

15.0 g (41 mmol) of the product from Method 6 are stirred with 2.1 g (42 mmol) of hydrazine hydrate in 150 ml of methanol for 2 hours at room temperature. The residue is again filtered off under suction, the mother liquor is evaporated down and triturated with diethyl ether, the residue is filtered off under suction and the mother liquor is evaporated down. 7.8 g (80% of theory) of an acid-sensitive oil remain.

¹ H-NMR (CDCl₃): δ=3.90 (s, 3H); 4.03 (s, 3H); 4.59 (s, 2H); 5.35 (sbr, 2H); 7.15 (dbr, 1H); 7.40 (sbr, 3H)

EXAMPLE 1

Methyl 3-methoxy-2-[2'-[1"-(3'", 5'"-dichlorophenyl)-1"-methyl]-iminooxymethyl]-phenylacrylate (No. 582, Table I)

0.6 g (25 mmol) of sodium hydride powder in 100 ml of acetonitrile is initially taken, 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added and the mixture is refluxed for 1 hour. Thereafter, 9.3 g (33 mmol) of methyl 2-(2'-bromomethyl)-phenyl-3-methoxyacrylate in 50 ml of acetonitrile are added dropwise and refluxing is continued for a further 4 hours. The mixture is evaporated down under reduced pressure and then partitioned between methyl tert-butyl ether and saturated ammonium chloride solution, the organic phase is washed with water and the residue obtained by evaporation is crystallized from methyl butyl ether/n-hexane. 4.6 g (45% of theory) of a substance of melting point 87°-88° C. are obtained.

¹ H-NMR (CDCl₃): δ=2.19 (s, 3H); 3.70 (s, 3H); 3.81 (s, 3H); 5.15 (s, 2H); 7.08 (m, 1H); 7.17 (m, 3H); 7.50 (m, 3H); 7.58 (s, 1H)

EXAMPLE 2

Methyl 3-methoxy-2-[2'-(1'-cyano-(-1"-methoxy-1"-methylethyl)-iminooxymethyl]-phenylacrylate (No. 36, Table I)

3.3 g (23 mmol) of 3-methoxy-3-methyl-2-oximinobutyronitrile, 6.6 g (23 mmol) of methyl 2-(2'-bromomethylphenyl)-3-methoxyacrylate and 3.2 g (23 mmol) of potassium carbonate in 60 ml of N,N-dimethylformamide are stirred for 15 hours at room temperature. The mixture is then evaporated down, the residue is taken up in ethyl acetate, the solution is washed with 3×50 ml of water and the organic phase is dried over sodium sulfate, evaporated down and chromatographed over silica gel using 40:1 toluene/ethyl acetate.

Yield: 7.0 g (88% of theory) of an oil.

IR (film): 1,285, 1,258, 1,189, 1,180, 1,131, 1,111, 1,069, 1,008 cm⁻¹.

EXAMPLE 3

Methyl 2-methoximino-2-[2'-(1"-(3'", 5'"-dichlorophenyl)-1"-methyl)-iminooxymethyl]-phenylacetate (No. 582, Table II)

0.6 g (25 mmol) of NaH in 50 ml of acetonitrile is initially taken, and 5.1 g (25 mmol) of 3,5-dichloroacetophenone oxime are added at room temperature. Refluxing is carried out for 1 hour, after which 9.4 g (33 mmol) of methyl 2-methoximino-2-(2'-bromomethyl)phenylacetate in 50 ml of acetonitrile are added dropwise and refluxing is continued for a further 4 hours. After evaporating down, partitioning the residue between water/methyl tert-butyl ether, washing the organic phase with water, drying the organic phase with sodium sulfate and evaporating down, the residue is subjected to column chromatography over silica gel using methyl tert-butyl ether/hexane. 5.4 g (53% of theory) of crystals of melting point 95°-97° C. result.

¹ H-NMR (CDCl₃): δ=2.17 (s, 3H); 3.82 (s, 3H); 4.02 (s, 3H); 5.15 (s, 2H); 7.20 (dbr, 1H); 7.25-7.55 (m, 6H)

EXAMPLE 4

Methyl 3-methoxy-2-[2'-(1"-(4'"-bromophenyl)-1"-methyl)-iminooxymethyl]-phenylacrylate (No. 593, Table I)

2.37 g (10 mmol) of methyl 3-methoxy-2-(2'-aminooxymethyl)-phenylacrylate, 1.99 g (10 mmol) of 4-bromoacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml of methanol are combined and the mixture is stirred for 24 hours at room temperature. The mixture is evaporated down, the residue is partitioned between water/methyl tert-butyl ether and the organic phase is washed with 2N HCl and washed neutral with NaHCO₃ and evaporated down, and the residue is chromatographed over SiO₂ using methyl tert-butyl ether/hexane. 2.1 g (51% of theory) of crystals of melting point 105°-107° C. result. ¹ H-NMR (CDCl₃): δ=2.22 (s, 3H); 3.70 (s, 3H); 3.80 (s, 3H); 5.15 (s, 2H); 7.16 (dbr, 1H); 7.33 (m, 2H); 7.45 (m, 5H); 7.58 (s, 1H)

EXAMPLE 5

Methyl 2-methoximino-2-[2'-(1"-(4'"-nitrophenyl)-1"-methyl)-iminooxymethyl]-phenylacetate (No. 614, Table II)

2.38 g (10 mmol) of methyl 2-methoximino-2-(2'-aminooxymethyl)-phenylacetate, 1.65 g (10 mmol) of 4-nitroacetophenone, 2 ml of water, 0.8 g of pyridine and 10 ml of methanol are reacted as in Example 4. 2.1 g (55% of theory) of crystals of melting point 87°-89° C. are obtained.

¹ H-NMR (CDCl₃): δ=2.22 (s, 3H); 3.81 (s, 3H); 4.02 (s, 3H); 5.18 (s, 2H); 7.20 (dd, 1H); 7.4 (m, 3H); 7.75 (dd, 2H); 8.18 (dd, 2H).

EXAMPLE 6

Methyl 3-methoxy-2-[2'-(1"-(4'"-chlorophenyl)-iminooxymethyl]-phenylacrylate (No. 95 Table 5)

a) 5.5 g (15 mmol) of methyl 3-methoxy-2-[2'-(phthalimidooxy)-methyl]-phenylacrylate (from Method 4 ) in 100 ml of methanol are initially taken, and 0.75 g (15 mmol) of hydrazine hydrate is added at room temperature. After 15 minutes at this temperature, the mixture is evaporated down, the residue is triturated with methyl tert-butyl ether and the cleavage product is filtered off under suction. The mother liquor is evaporated down, the residue is taken up with 50 ml of methanol and 2.1 g (15 mmol) of 4-chlorobenzaldehyde in 50 ml of methanol plus 1 drop of pyridine are added dropwise.

Stirring was carried out overnight at 23° C., after which the product was filtered off under suction, washed with methanol and dried.

2.9 g (54% of theory) of crystals of melting point 87°-89° C. were obtained.

¹ H-NMR (CDCl₃): δ=3.66 (s, 3H); 3.80 (s, 3H); 5.13 (s, 2H); 7.17 (m, 1H); 7.35 (m, 4H); 7.50 (me, 3H); 7.60 (s, 1H); 8.06 (s, 1H).

b) 50 ml of methanol are slowly added to 1.3 g (55 mmol) of NaH powder under a nitrogen atmosphere (evolution of hydrogen). 7.8 g (50 mmol) of 4-chlorobenzaldehyde oxime in 50 ml of methanol are then added at room temperature. Stirring is carried out for half an hour, after which 14.3 g (50 mmol) of methyl 3-methoxy-2-(2'-bromomethyl)-phenylacrylate in 50 ml of methanol are added dropwise and stirring is carried out at room temperature for a further 48 hours. The white residue is filtered off under suction, washed with methanol and dried. 1.9 g (11% of theory) of a product of melting point 82°-84° C. are obtained.

EXAMPLE 7

Methyl 2-methoximino-2-(2'-phthalimidooxymethyl)-phenylacetate (No. 1, Table 8)

2.0 g (7 mmol) of methyl 2-methoxyimino-2-(2'-bromomethyl)-phenylacetate, 1.1 g (7 mmol) of hydroxyphthalimide and 0.8 g (7.7 mmol) of triethylamine are dissolved in 10 ml of N-methylpyrrolidone and the mixture is stirred for 2 hours at 70 ° C. Ice water is added and the crystals are filtered off under suction, washed with water and methyl tert-butyl ether and dried. There remain 1.5 g (58% of theory) of crystals of melting point 152°-155° C. ¹ H-NMR (CDCl₃): δ=3.83 (s, 3H); 3.98 (s, 3H); 5.07 (s, 2H); 7.15 (dbr, 1H); 7.45 (mc, 2H); 7.60-7.85 (m, 5H).

The compounds listed in Tables I-IX can be prepared in a similar manner.

                                      TABLE I                                      __________________________________________________________________________      ##STR13##                                                                     No. R.sup.3      R.sup.4            Data                                       __________________________________________________________________________      1  Cl           Phenyl                                                         2  Cl           Cyano                                                          3  Cl           Ethoxycarbonyl                                                 4  Cl           Cyclopropyl                                                    5  CF.sub.3     CF.sub.3                                                       6  CF.sub.3     Phenyl                                                         7  CCl.sub.3    CCl.sub.3                                                      8  CCl.sub.3    Phenyl                                                         9  CH.sub.2 Cl  Phenyl                                                         10 CF.sub.2 CF.sub.3                                                                           Phenyl                                                         11 CF.sub.2 Cl  Phenyl                                                         12 CHCl.sub.2   Phenyl                                                         13 Cyclopropyl  Cyclopropyl                                                    14 Cyclopropyl  Phenyl             oil; IR (film): 1190, 1129, 1056,                                              1032, 768                                   15 Cyclopropyl  4-Fluorophenyl     oil; IR (film): 1508, 1225, 1129,                                              998, 839                                    16 Cyclopropyl  4-Chlorophenyl     oil; IR (film): 1490, 1129, 1091,                                              1014, 1800                                  17 Cyclopropyl  4-Methoxyphenyl    oil; IR (film): 1251, 1177, 1129,                                              1033                                        18 Cyclopropyl  4-Ethoxyphenyl                                                 19 Cyclopropyl  4-Phenoxyphenyl                                                20 Cyclopropyl  Pentachlorophenyl                                              21 Cyclopropyl  Pentafluorophenyl                                              22 Cyclopentyl  Phenyl                                                         23 Cyclohexyl   Phenyl                                                         24 Phenyl       2,2-Dichloro-1-methylcyclopropyl                               25 Phenyl       2,2-Difluorocyclopropyl                                        26 Phenyl       2,2-Dichlorocyclopropyl                                        27 Phenyl       2,2-Dibromocyclopropyl                                         28 Phenyl       2,2,3,3-Tetrafluorocyclobutyl                                  29 Phenyl       2,2-Dimethylcyclopropyl                                        30 Phenyl       1-Methylcyclohexyl                                             31 CN           Methoxymethyl                                                  32 CN           Ethoxymethyl                                                   33 CN           n-Propoxymethyl                                                34 CN           iso-Propoxymethyl                                              35 CN           tert.-Butoxymethyl                                             36 CN           2-Methoxyprop-2-yl oil; IR (film): 1436, 1191, 1131,                                              1057, 1003                                  37 CN           2-Ethoxyprop-2-yl  oil; IR (film): 1191, 1177, 1131,                                              1095, 1010                                  38 CN           2-n-Propoxyprop-2-yl                                                                              oil; IR (film): 1191, 1175, 1131,                                              1060, 1005                                  39 CN           2-iso-Propoxyprop-2-yl                                                                            oil; IR (film): 1370, 1191, 1172,                                              1131, 998                                   40 CN           2-tert.-Butoxyprop-2-yl                                        41 CN           Methylthiomethyl                                               42 CN           tert.-Butylthiomethyl                                          43 CN           2-Methylthioprop-2-yl                                                                             oil; IR (film): 1436, 1191, 1131,                                              1114, 1016, 998                             44 CN           2-iso-Propylthioprop-2-yl                                      45 CN           2-tert.-Butylthioprop-2-yl                                                                        oil; IR (film): 1366, 1191, 1132,                                              1113, 1012, 1000                            46 CN           Methyl                                                         47 CN           Ethyl                                                          48 CN           n-Propyl                                                       49 CN           iso-Propyl         oil; IR (film): 1285, 1258, 1189,                                              1131, 1111, 1069, 1008                      50 CN           n-Butyl                                                        51 CN           iso-Butyl                                                      52 CN           sec.-Butyl                                                     53 CN           tert.-Butyl                                                    54 CN           n-Hexyl                                                        55 CN           n-Decyl                                                        56 CN           Cyclopropyl        oil; IR (film): 1207, 1190, 1130,                                              1057, 1003                                  57 CN           Cyclohexyl                                                     58 CN           Phenylthiomethyl                                               59 CN           2-Phenylthiomethyl                                             60 CN           2-(2'-Chlorophenylthio)prop-2-yl                               61 CN           Ethynyl                                                        62 CN           1-Propynyl                                                     63 CN           Methoxy                                                        64 CN           Ethoxy                                                         65 CN           n-Propoxy                                                      66 CN           iso-Propoxy                                                    67 CN           n-Butoxy                                                       68 CN           iso-Butoxy                                                     69 CN           sec.-Butoxy                                                    70 CN           tert.-Butoxy                                                   71 CN           Methylthio                                                     72 CN           Ethylthio                                                      73 CN           n-Propylthio                                                   74 CN           iso-Propylthio                                                 75 CN           n-Butylthio                                                    76 CN           iso-Butylthio                                                  77 CN           sec.-Butylthio                                                 78 CN           tert.-Butylthio                                                79 CN           Benzylthio                                                     80 CN           Trifluoromethoxy                                               81 CN           Cyano                                                          82 CN           Amino                                                          83 CN           Methylamino                                                    84 CN           Dimethylamino                                                  85 CN           Ethylamino                                                     86 CN           Diethylamino                                                   87 CN           Di-n-Propylamino                                               88 CN           Di-iso-Propylamino                                             89 CN           Di-n-Butylamino                                                90 CN           Di-iso-Butylamino                                              91 CN           Acetyl                                                         92 CN           Propion-1-yl                                                   93 CN           Butyr-1-yl                                                     94 CN           iso-Butyr-1-yl                                                 95 CN           Pivaloyl                                                       96 CN           Benzoyl                                                        97 CN           4-Chlorobenzoyl                                                98 CN           Benzylcarbonyl                                                 99 CN           Methoxycarbonyl                                               100 CN           Ethoxycarbonyl                                                101 CN           n-Propoxycarbonyl                                             102 CN           iso-Propoxycarbonyl                                           103 CN           n-Butoxycarbonyl                                              104 CN           iso-Butoxycarbonyl                                            105 CN           sec.-Butoxycarbonyl                                           106 CN           tert.-Butoxycarbonyl                                          107 CN           n-Hexoxycarbonyl                                              108 CN           Phenoxycarbonyl                                               109 CN           4-Chlorophenoxycarbonyl                                       110 CN           Benzyloxycarbonyl                                             111 CN           Aminocarbonyl                                                 112 CN           Dimethylaminocarbonyl                                         113 CN           Diethylaminocarbonyl                                          114 CN           Di-iso-Propylaminocarbonyl                                    115 CN           Phenylaminocarbonyl                                           116 CN           N-Methyl-N-Phenylaminocarbonyl                                117 CN           Phenyl             oil; IR (film): 1245, 1127, 1024,                                              1015, 767, 750                             118 CN           2-Fluorophenyl                                                119 CN           3-Fluorophenyl                                                120 CN           4-Fluorophenyl                                                121 CN           Pentafluorophenyl                                             122 CN           2-Chlorophenyl                                                123 CN           3-Chlorophenyl                                                124 CN           4-Chlorophenyl                                                125 CN           Pentachlorophenyl                                             126 CN           2,3-Dichlorophenyl                                            127 CN           2,4-Dichlorophenyl                                            128 CN           2,5-Dichlorophenyl                                            129 CN           2,6-Dichlorophenyl                                            130 CN           3,4-Dichlorophenyl                                            131 CN           3,5-Dichlorophenyl                                            132 CN           2,3,4-Trichlorophenyl                                         133 CN           2,3,5-Trichlorophenyl                                         134 CN           2,3,6-Trichlorophenyl                                         135 CN           2,4,5-Trichlorophenyl                                         136 CN           2,4,6-Trichlorophenyl                                         137 CN           3,4,5-Trichlorophenyl                                         138 CN           2,3,4,6-Tetrachlorophenyl                                     139 CN           2,3,5-6-Tetrachlorophenyl                                     140 CN           2-Bromophenyl                                                 141 CN           3-Bromophenyl                                                 142 CN           4-Bromophenyl                                                 143 CN           2,4-Dibromophenyl                                             144 CN           3-Bromo-4-fluorophenyl                                        145 CN           3-Bromo-4-methoxyphenyl                                       146 CN           2-Iodophenyl                                                  147 CN           3-Iodophenyl                                                  148 CN           4-Iodophenyl                                                  149 CN           2-Chloro-4-fluorophenyl                                       150 CN           2-Chloro-5-fluorophenyl                                       151 CN           2-Chloro-6-fluorophenyl                                       152 CN           2-Chloro-4-bromophenyl                                        153 CN           2-Bromo-4-chlorophenyl                                        154 CN           2-Bromo-4-fluorophenyl                                        155 CN           3-Bromo-4-chlorophenyl                                        156 CN           3-Chloro-4-fluorophenyl                                       157 CN           3-Fluoro-4-chlorophenyl                                       158 CN           2-Cyanophenyl                                                 159 CN           3-Cyanophenyl                                                 160 CN           4-Cyanophenyl                                                 161 CN           2-Nitrophenyl                                                 162 CN           3-Nitrophenyl                                                 163 CN           4-Nitrophenyl                                                 164 CN           2-Methylphenyl                                                165 CN           3-Methylphenyl                                                166 CN           4-Methylphenyl                                                167 CN           2,4-Dimethylphenyl                                            168 CN           2,6-Dimethylphenyl                                            169 CN           3,4-Dimethylphenyl                                            170 CN           3,5-Dimethylphenyl                                            171 CN           2,3,4-Trimethylphenyl                                         172 CN           2,3,5-Trimethylphenyl                                         173 CN           2,3,6-Trimethylphenyl                                         174 CN           2,4,5-Trimethylphenyl                                         175 CN           2,4,6-Trimethylphenyl                                         176 CN           3,4,5-Trimethylphenyl                                         177 CN           Pentamethylphenyl                                             178 CN           2-Ethylphenyl                                                 179 CN           3-Ethylphenyl                                                 180 CN           4-Ethylphenyl                                                 181 CN           3,5-Diethylphenyl                                             182 CN           2-n-Propylphenyl                                              183 CN           3-n-Propylphenyl                                              184 CN           4-n-Propylphenyl                                              185 CN           2-iso-Propylphenyl                                            186 CN           3-iso-Propylphenyl                                            187 CN           4-iso-Propylphenyl                                            188 CN           2,4-Di-iso-Propylphenyl                                       189 CN           3,5-Di-iso-Propylphenyl                                       190 CN           4-n-Butylphenyl                                               191 CN           4-sec.-Butylphenyl                                            192 CN           4-iso-Butylphenyl                                             193 CN           4-tert.-Butylphenyl                                           194 CN           3-tert.-Butylphenyl                                           195 CN           2-tert.-Butylphenyl                                           196 CN           2,4-Di-tert.-Butylphenyl                                      197 CN           3,5-Di-tert.-Butylphenyl                                      198 CN           4-n-Hexylphenyl                                               199 CN           4-n-Dodecylphenyl                                             200 CN           2-Methyl-4-tert.-Butylphenyl                                  201 CN           2-Methyl-6-tert.-Butylphenyl                                  202 CN           2-Methyl-4-iso-Propylphenyl                                   203 CN           2-Methyl-4-Cyclohexylphenyl                                   204 CN           2-Methyl-4-Phenylphenyl                                       205 CN           2-Methyl-4-Benzylphenyl                                       206 CN           2-Methyl-4-Phenoxyphenyl                                      207 CN           2-Methyl-4-Benzyloxyphenyl                                    208 CN           2-Methyl-3-Chlorophenyl                                       209 CN           2-Methyl-4-Chlorophenyl                                       210 CN           2-Methyl-5-Chlorophenyl                                       211 CN           2-Methyl-6-Chlorophenyl                                       212 CN           2-Methyl-4-Fluorophenyl                                       213 CN           2-Methyl-3-Bromophenyl                                        214 CN           2-Methyl-4-Bromophenyl                                        215 CN           2-Methyl-3-Methoxyphenyl                                      216 CN           2-Methyl-4-Methoxyphenyl                                      217 CN           2-Methyl-5-methoxyphenyl                                      218 CN           2-Methyl-6-methoxyphenyl                                      219 CN           2-Methyl-4-iso-Propoxyphenyl                                  220 CN           2-Methyl-2,5-dimethoxyphenyl                                  221 CN           2-Methoxyphenyl                                               222 CN           3-Methoxyphenyl                                               223 CN           4-Methoxyphenyl                                               224 CN           2,3-Dimethoxyphenyl                                           225 CN           2,4-Dimethoxyphenyl                                           226 CN           2,5-Dimethoxyphenyl                                           227 CN           2,6-Dimethoxyphenyl                                           228 CN           3,4-Dimethoxyphenyl                                           229 CN           3,5-Dimethoxyphenyl                                           230 CN           3,6-Dimethoxyphenyl                                           231 CN           2,3,4-Trimethoxyphenyl                                        232 CN           2,3,5-Trimethoxyphenyl                                        233 CN           2,3,6-Trimethoxyphenyl                                        234 CN           2,4,5-Trimethoxyphenyl                                        235 CN           2,4,6-Trimethoxyphenyl                                        236 CN           3,4,5-Trimethoxyphenyl                                        237 CN           2-Ethoxyphenyl                                                238 CN           3-Ethoxyphenyl                                                239 CN           4-Ethoxyphenyl                                                240 CN           2-iso-Propoxyphenyl                                           241 CN           3-iso-Propoxyphenyl                                           242 CN           4-iso-Propoxyphenyl                                           243 CN           3-tert.-Butoxyphenyl                                          244 CN           4-tert.-Butoxyphenyl                                          245 CN           2-Trifluoromethoxyphenyl                                      246 CN           3-Trifluoromethoxyphenyl                                      247 CN           4-Trifluoromethoxyphenyl                                      248 CN           3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                       249 CN           4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                       250 CN           2-Chloromethylphenyl                                          251 CN           3-Chloromethylphenyl                                          252 CN           4-Chloromethylphenyl                                          253 CN           2-Trifluoromethylphenyl                                       254 CN           3-Trifluoromethylphenyl                                       255 CN           4-Trifluoromethylphenyl                                       256 CN           2-(Methoxyiminomethyl)phenyl                                  257 CN           3-(Methoxyiminomethyl)phenyl                                  258 CN           4-(Methoxyiminomethyl)phenyl                                  259 CN           2-(Ethoxyiminomethyl)phenyl                                   260 CN           3-(Ethoxyiminomethyi)phenyl                                   261 CN           4-(Ethoxyiminomethyl)phenyl                                   262 CN           2-(n-Propoxyiminomethyl)phenyl                                263 CN           3-(n-Propoxyiminomethyl)phenyl                                264 CN           4-(n-Propoxyiminomethyl)phenyl                                265 CN           2-(iso-Propoxyiminomethyl)phenyl                              266 CN           3-(iso-Propoxyiminomethyl)phenyl                              267 CN           4-(iso-Propoxylminomethyl)phenyl                              268 CN           2-(n-Butoxyiminomethyl)phenyl                                 269 CN           3-(n-Butoxylminomethyl)phenyl                                 270 CN           4-(n-Butoxyiminomethyl)phenyl                                 271 CN           2-(iso-Butoxyiminomethyl)phenyl                               272 CN           3-(iso-Butoxylminomethyl)phenyl                               273 CN           4-(iso-Butoxyiminomethyl)phenyl                               274 CN           2-(tert.-Butoxyiminomethyl)phenyl                             275 CN           3-(tert.-Butoxylminomethyl)phenyl                             276 CN           4-(tert.-Butoxylminomethyl)phenyl                             277 CN           2-(n-Pentoxyiminomethyl)phenyl                                279 CN           4-(n-Pentoxyiminomethyl)phenyl                                280 CN           2-(n-Hexoxyiminomethyl)phenyl                                 281 CN           3-(n-Hexoxyiminomethyl)phenyl                                 282 CN           4-(n-Hexoxyiminomethyl)phenyl                                 283 CN           2-(Allyloxyiminomethyl)phenyl                                 284 CN           3-(Allyloxyiminomethyl)phenyl                                 285 CN           4-(Allyloxyiminomethyl)phenyl                                 286 CN           2-(Benzyloxyiminomethyl)phenyl                                287 CN           3-(Benzyloxyiminomethyl)phenyl                                288 CN           4-(Benzyloxyiminomethyl)phenyl                                289 CN           2-(Methoxyimino-1'-ethyl)phenyl                               290 CN           3-(Methoxyimino-1'-ethyl)phenyl                               291 CN           4-(Methoxyimino-1'-ethyl)phenyl                               292 CN           2-(Ethoxyimino-1'-ethyl)phenyl                                293 CN           3-(Ethoxyimino-1'-ethyl)phenyl                                294 CN           4-(Ethoxyimino-1'-ethyl)phenyl                                295 CN           2-(n-Propoxyimino-1'-ethyl)phenyl                             296 CN           3-(n-Propoxyimino-1'-ethyl)phenyl                             297 CN           4-(n-Propoxyimino-1'-ethyl)phenyl                             298 CN           2-(n-Butoxyamino-1'-ethyl)phenyl                              299 CN           3-(n-Butoxyamino-1'-ethyl)phenyl                              300 CN           4-(n-Butoxyamino-1'-ethyl)phenyl                              301 CN           2-(n-Pentoxyimino-1'-ethyl)phenyl                             302 CN           3-(n-Pentoxyimino-1'-ethyl)phenyl                             303 CN           4-(n-Pentoxyimino-1'-ethyl)phenyl                             304 CN           2-(n-Hexoxyimino-1'-ethyl)phenyl                              305 CN           3-(n-Hexoxyimino-1'-ethyl)phenyl                              306 CN           4-(n-Hexoxyimino-1'-ethyl)phenyl                              307 CN           2-(Allyloxyimino-1'-ethyl)phenyl                              308 CN           3-(Allyloxyimino-1'-ethyl)phenyl                              309 CN           4-(Allyloxyimino-1'-ethyl)phenyl                              310 CN           2-(Benzyloxyimino-1'-ethyl)phenyl                             311 CN           3-(Benzyloxyimino-1'-ethyl)phenyl                             312 CN           4-(Benzyloxyimino-1'-ethyl)phenyl                             313 CN           2-Phenylphenyl                                                314 CN           3-Phenylphenyl                                                315 CN           4-Phenylphenyl                                                316 CN           2-Phenoxyphenyl                                               317 CN           3-Phenoxyphenyl                                               318 CN           4-Phenoxyphenyl                                               319 CN           2-Benzyloxyphenyl                                             320 CN           3-Benzyloxyphenyl                                             321 CN           4-Benzyloxyphenyl                                             322 CN           4-(Imidazol-1'-yl)phenyl                                      323 CN           4-(Piperazin-1'-yl)phenyl                                     324 CN           4-(Morpholin-1'-yl)phenyl                                     325 CN           4-(Piperidin-1'-yl)phenyl                                     326 CN           4-(Pyridyl-2'-oxy)phenyl                                      327 CN           2-Cyclopropylphenyl                                           328 CN           3-Cyclopropylphenyl                                           329 CN           4-Cyclopropylphenyl                                           330 CN           3-Cyclohexylphenyl                                            331 CN           4-Cyclohexylphenyl                                            332 CN           4-Oxiranylphenyl                                              333 CN           4-(1',3'-Dioxan-2'-yl)phenyl                                  334 CN           4-(Tetrahydropyran-2-yloxy)phenyl                             335 CN           1-Naphthyl                                                    336 CN           2-Naphthyl                                                    337 CN           9-Anthryl                                                     338 CN           1-Naphtoxy                                                    339 CN           2-Naphtoxy                                                    340 CN           9-Anthroxy                                                    341 CN           Phenoxy                                                       342 CN           2-Chlorophenoxy                                               343 CN           3-Chlorophenoxy                                               344 CN           4-Chlorophenoxy                                               345 CN           4-Methylphenoxy                                               346 CN           4-tert.-Butylphenoxy                                          347 CN           4-Methoxyphenoxy                                              348 CN           4-Ethoxyphenoxy                                               349 CN           4-tert.-Butoxyphenoxy                                         350 CN           Phenylthio                                                    351 CN           2-Chlorophenylthio                                            352 CN           4-Chlorophenylthio                                            353 CN           Benzyl                                                        354 CN           2-Methylbenzyl                                                355 CN           3-Methylbenzyl                                                356 CN           4-Methylbenzyl                                                357 CN           4-tert.-Butylbenzyl                                           358 CN           2-Chlorobenzyl                                                359 CN           3-Chlorobenzyl                                                360 CN           4-Chlorobenzyl                                                361 CN           2,4-Dichlorobenzyl                                            362 CN           2,6-Dichiorobenzyl                                            363 CN           2,4,6-Trichlorobenzyl                                         364 CN           2-Trifluoromethylbenzyl                                       365 CN           3-Trifluoromethylbenzyl                                       366 CN           4-Trifluoromethylbenzyl                                       367 CN           2-Methoxybenzyl                                               368 CN           4-Methoxybenzyl                                               369 CN           4-tert.-Butoxybenzyl                                          370 CN           4-Phenoxybenzyl                                               371 CN           1-Phenethyl                                                   372 CN           2-Phenethyl                                                   373 CN           1-Phenylpropyl                                                374 CN           2-Phenylpropyl                                                375 CN           3-Phenylpropyl                                                376 CN           2-Methyl-2-phenylpropyl                                       377 CN           2-methyl-3-phenylpropyl                                       378 CN           4-Phenylbutyl                                                 379 CN           2-Phenyl-1-ethenyl                                            380 CN           1-Phenyl-1-ethenyl                                            381 CN           1-Phenyl-1-propenyl                                           382 CN           1-Phenyl-1-propen-2-yl                                        383 CN           2,2-Diphenylethenyl                                           384 CN           Phenoxymethyl                                                 385 CN           2-Pyridyl                                                     386 CN           3-Pyridyl                                                     387 CN           4-Pyridyl                                                     388 CN           2,6-Pyrimidinyl                                               389 CN           1,5-Pyrimidinyl                                               390 CN           2-Thienyl                                                     391 CN           3-Thienyl                                                     392 CN           2-Furyl                                                       393 CN           3-Furyl                                                       394 CN           1-Pyrrolyl                                                    395 CN           1-Imidazolyl                                                  396 CN           1,2,4-Triazolyl                                               397 CN           1,3,4-Triazolyl                                               398 CN           4-Thiazolyl                                                   399 CN           2-Benzothiazolyl                                              400 CN           2-Pyridyloxy                                                  401 CN           2-Pyrimidinyloxy                                              402 CN           2-Pyridylthio                                                 403 CN           2-Pyrimidinylthio                                             404 CN           2-Benzothiazolylthio                                          405 CN           Phenylthiomethyl                                              406 CN           2-Pyridylmethyl                                               407 CN           3-Pyridylmethyl                                               408 CN           Furfuryloxy                                                   409 CN           Thienylmethoxy                                                410 CN           3-Isoxazolylmethoxy                                           411 CN           2-Oxazolylmethoxy                                             412 CN           2-Pyridylmethoxy                                              413 CN           2'-Furyl-2-ethenyl                                            414 CN           2'-Thienyl-2-ethenyl                                          415 CN           3'-Pyridyl-2-ethenyl                                          416 CN           Oxiranyl                                                      417 CN           1-Aziridinyl                                                  418 CN           1-Azetidinyl                                                  419 CN           1-Pyrrolidinyl                                                420 CN           2-Tetrahydrofuryl                                             421 CN           2-Tetrahydropyranyl                                           422 CN           3-Tetrahydropyranyl                                           423 CN           1-Piperidinyl                                                 424 CN           1-Morpholinyl                                                 425 CN           1-Piperazinyl                                                 426 CN           1,3-Dioxan-2-yl                                               427 CN           3-Tetrahydrothiopyranyl                                       428 CN           2-Dihydropyranytoxy                                           429 CN           2-Tetrahydropyranytoxy                                                                            oil; IR (film): 12051131, 1087, 1047,                                          1004                                       430 CN           (CH.sub.2).sub.4                                              431 CN           (CH.sub.2).sub.5                                              432 CN           (CH.sub.2).sub.6                                              433 CN                                                                         434 CN                                                                         435 CN                                                                                           ##STR14##                                                    436 CN                                                                                           ##STR15##                                                    437 CN                                                                                           ##STR16##                                                    438 CN                                                                                           ##STR17##                                                    439 CN                                                                                           ##STR18##                                                    440 CN                                                                                           ##STR19##                                                    441 CN           CF.sub.3                                                      442 CN           2-Fluoroethyl                                                 443 CN           2,2,2-Trifluoroethyl                                          444 CN           Pentafluoroethyl                                              445 CN           Chloromethyl                                                  446 CN           Dichloromethyl                                                447 CN           Trichloromethyl                                               448 CN           2-Chloroethyl                                                 449 CN           2,2,2-Trichloroethyl                                          450 CN           Pentachloroethyl                                              451 CN           Cyclopropyl                                                   452 CN           Cyclobutyl                                                    453 CN           Cyclopentyl                                                   454 CN           Cyclohexyl                                                    455 CN           1-Methylcyclopropyl                                           456 CN           2,2-Dimethylcyclopropyl                                       457 CN           1-Methylcyclohexyl                                            458 CN           2,2-Difluorocyclopropyl                                       459 CN           2,2-Dichlorocyclopropyl                                       460 CN           2,2-Dibromocyclopropyl                                        461 CN           2,2-Dichloro-3-methylcyclopropyl                              462 CN           2,2,3,3-Tetrafluorocyclobutyl                                 463 CN           Ethenyl                                                       464 CN           1-Propenyl                                                    465 CN           2-Methyl-1-propenyl                                           466 CN           4-Methylpent-3-en-1-yl                                        467 CN           2-Propenyl                                                    468 CN           2-Butenyl                                                     469 CN           1-Methyl-2-propenyl                                           470 CN           3-Methyl-2-butenyl                                            471 CN           2,2-Difluoroethenyl                                           472 CN           2,2-Dichloroethenyl                                           473 CN           3,3,3-Trifluoropropenyl                                       474 CN           3,3,3-Trichloropropenyl                                       475 CN           3-Chloro-2-propenyl                                           476 CN           Cyclopent-1-enyl                                              477 CN           Cyclopentadienyl                                              478 CN           Cyclohex-1-enyl                                               479 CN           Pentafluorocyclopentadienyl                                   480 CN           Pentachlorocyclopentadienyl                                   481 CN           Styryl                                                        482 CH.sub.3     Methoxymethyl                                                 483 CH.sub.3     Ethoxymethyl                                                  484 CH.sub.3     n-Propoxymethyl                                               485 CH.sub.3     iso-Propoxymethyl                                             486 CH.sub.3     tert.-Butoxymethyl                                            487 CH.sub.3     2-Methoxyprop-2-yl                                            488 CH.sub.3     2-Ethoxyprop-2-yl                                             489 CH.sub.3     2-n-Propoxyprop-2-yl                                          490 CH.sub.3     2-iso-Propoxyprop-2-yl                                        491 CH.sub.3     2-tert.-Butoxyprop-2-yl                                       492 CH.sub.3     Methylthiomethyl                                              493 CH.sub.3     tert.-Butylthiomethyl                                         494 CH.sub.3     2-Methylthioprop-2-yl                                         495 CH.sub.3     2-iso-Propylthioprop-2-yl                                     496 CH.sub.3     2-tert.-Butylthioprop-2-yl                                    497 CH.sub.3     Methyl                                                        498 CH.sub.3     Ethyl                                                         499 CH.sub.3     n-Propyl                                                      500 CH.sub.3     iso-Propyl                                                    501 CH.sub.3     n-Butyl                                                       502 CH.sub.3     iso-Butyl                                                     503 CH.sub.3     sec.-Butyl                                                    504 CH.sub.3     tert.-Butyl                                                   505 CH.sub.3     n-Hexyl                                                       506 CH.sub.3     n-Decyl                                                       507 CH.sub.3     Cyclopropyl                                                   508 CH.sub.3     Cyclohexyl                                                    509 CH.sub.3     Phenylthiomethyl                                              510 CH.sub.3     2-Phenylthiomethyl                                            511 CH.sub.3     2-(2'-Chlorophenylthio)prop-2-yl                              512 CH.sub.3     Ethynyl                                                       513 CH.sub.3     1-Propynyl                                                    514 CH.sub.3     Methoxy                                                       515 CH.sub.3     Ethoxy                                                        516 CH.sub.3     n-Propoxy                                                     517 CH.sub.3     iso-Propoxy                                                   518 CH.sub.3     n-Butoxy                                                      519 CH.sub.3     iso-Butoxy                                                    520 CH.sub.3     sec.-Butoxy                                                   521 CH.sub.3     tert.-Butoxy                                                  522 CH.sub.3     methylthio                                                    523 CH.sub.3     Ethylthio                                                     524 CH.sub.3     n-Propylthio                                                  525 CH.sub.3     iso-Propylthio                                                526 CH.sub.3     n-Butylthio                                                   527 CH.sub.3     iso-Butylthio                                                 528 CH.sub.3     sec.-Butylthio                                                529 CH.sub.3     tert.-Butylthio                                               530 CH.sub.3     Benzylthio                                                    531 CH.sub.3     Trifluoromethoxy                                              532 CH.sub.3     Cyano                                                         533 CH.sub.3     Amino                                                         534 CH.sub.3     Methylamino                                                   535 CH.sub.3     Dimethylamino                                                 536 CH.sub.3     Ethylamino                                                    537 CH.sub.3     Diethylamino                                                  538 CH.sub.3     Di-n-Propylamino                                              539 CH.sub.3     Di-iso-Propylamino                                            540 CH.sub.3     Di-n-Butylamino                                               541 CH.sub.3     Di-iso-Butylamino                                             542 CH.sub.3     Acetyl                                                        543 CH.sub.3     Propion-1-yl                                                  544 CH.sub.3     Butyr-1-yl                                                    545 CH.sub.3     iso-Butyr-1-yl                                                546 CH.sub.3     Pivaloyl                                                      547 CH.sub.3     Benzoyl                                                       548 CH.sub.3     4-Chlorobenzoyl                                               549 CH.sub.3     Benzylcarbonyl                                                550 CH.sub.3     Methoxycarbonyl                                               551 CH.sub.3     Ethoxycarbonyl                                                552 CH.sub.3     n-Propoxycarbonyl                                             553 CH.sub.3     iso-Propoxycarbonyl                                           554 CH.sub.3     n-Butoxycarbonyl                                              555 CH.sub.3     iso-Butoxycarbonyl                                            556 CH.sub.3     sec.-Butoxycarbonyl                                           557 CH.sub.3     tert.-Butoxycarbonyl                                          558 CH.sub.3     n-Hexoxycarbonyl                                              559 CH.sub.3     Phenoxycarbonyl                                               560 CH.sub.3     4-Chlorophenoxycarbonyl                                       561 CH.sub.3     Benzyloxycarbonyl                                             562 CH.sub.3     Aminocarbonyl                                                 563 CH.sub.3     Dimethylaminocarbonyl                                         564 CH.sub.3     Diethylaminocarbonyl                                          565 CH.sub.3     Di-iso-Propylaminocarbonyl                                    566 CH.sub.3     Phenylaminocarbonyl                                           567 CH.sub.3     N-Methyl-N-Phenylaminocarbonyl                                568 CH.sub.3     Phenyl                                                        569 CH.sub.3     2-Fluorophenyl     oil; IR (film): 1708, 1634, 1257,                                              1129, 761                                  570 CH.sub.3     3-Fluorophenyl                                                571 CH.sub.3     4-Fluorophenyl     m.p.: 67-68° C.;                    572 CH.sub.3     Pentafluorophenyl                                             573 CH.sub.3     2-Chlorophenyl     oil.: --                                   574 CH.sub.3     3-Chlorophenyl                                                575 CH.sub.3     4-Chlorophenyl                                                576 CH.sub.3     Pentachlorophenyl                                             577 CH.sub.3     2,3-Dichlorophenyl                                            578 CH.sub.3     2,4-Dichlorophenyl oil; IR (film): 1708, 1634, 1256,                                              1129                                       579 CH.sub.3     2,5-Dichlorophenyl m.p.: 80-2° C.;                                                         IR; (KBr): 1704, 1634, 1250, 1132,                                             934, 766                                   580 CH.sub.3     2,6-Dichlorophenyl                                            581 CH.sub.3     3,4-Dichlorophenyl                                            582 CH.sub.3     3,5-Dichlorophenyl m.p.: 87-88° C.;                                                        IR (KBr): 1699, 1303, 1071, 1015,                                              932, 835                                   583 CH.sub.3     2,3,4-Trichlorophenyl                                                                             oil; IR (film): 1709, 1627, 1257,                                              1131, 1109                                 584 CH.sub.3     2,3,5-Trichlorophenyl                                         585 CH.sub.3     2,3,6-Trichlorophenyl                                         586 CH.sub.3     2,4,5-Trichlorophenyl                                         587 CH.sub.3     2,4,6-Trichlorophenyl                                         588 CH.sub.3     3,4,5-Trichlorophenyl                                         589 CH.sub.3     2,3,4,6-Tetrachlorophenyl                                     590 CH.sub.3     2,3,5,6-Tetrachlorophenyl                                     591 CH.sub.3     2-Bromophenyl                                                 592 CH.sub.3     3-Bromophenyl      m.p.: 60-2° C.;                                                         IR (KBr): 1708, 1635, 1253, 1129,                                              1113, 933, 773                             593 CH.sub.3     4-Bromophenyl      m.p.: 104-6° C.;                                                        IR (KBr): 1694, 1620, 1296, 1264,                                              1035, 938                                  594 CH.sub.3     2,4-Dibromophenyl                                             595 CH.sub.3     3-Bromo-4-Fluorophenyl                                        596 CH.sub.3     3-Bromo-4-Methoxyphenyl                                       597 CH.sub.3     2-iodophenyl                                                  598 CH.sub.3     3-iodophenyl                                                  599 CH.sub.3     4-iodophenyl                                                  600 CH.sub.3     2-Chloro-4-fluorophenyl                                       601 CH.sub.3     2-Chloro-5-fluorophenyl                                       602 CH.sub.3     2-Chloro-6-fluorophenyl                                       603 CH.sub.3     2-Chloro-4-bromophenyl                                        604 CH.sub.3     2-Bromo-4-chlorophenyl                                        605 CH.sub.3     2-Bromo-4-fluorophenyl                                        606 CH.sub.3     3-Bromo-4-chlorophenyl                                        607 CH.sub.3     3-Chloro-4-fluorophenyl                                       608 CH.sub.3     3-Fluoro-4-chlorophenyl                                       609 CH.sub.3     2-Cyanophenyl                                                 610 CH.sub.3     3-Cyanophenyl                                                 611 CH.sub.3     4-Cyanophenyl                                                 612 CH.sub.3     2-Nitrophenyl                                                 613 CH.sub.3     3-Nitrophenyl                                                 614 CH.sub.3     4-Nitrophenyl                                                 615 CH.sub.3     2-Methylphenyl                                                616 CH.sub.3     3-Methylphenyl     oil; IR (film): 1709, 1634, 1256,                                              1129                                       617 CH.sub.3     4-Methylphenyl     m.p.: 73-75° C.;                                                        IR (KBr): 1696, 1625, 1262, 1127,                                              1037, 930                                  618 CH.sub.3     2,4-Dimethylphenyl                                            619 CH.sub.3     2,6-Dimethylphenyl                                            620 CH.sub.3     3,4-Dimethylphenyl                                            621 CH.sub.3     3,5-Dimethylphenyl                                            622 CH.sub.3     2,3,4-Trimethylphenyl                                         623 CH.sub.3     2,3,5-Trimethylphenyl                                         624 CH.sub.3     2,3,6-Trimethylphenyl                                         625 CH.sub.3     2,4,5-Trimethylphenyl                                         626 CH.sub.3     2,4,6-Trimethylphenyl                                         627 CH.sub.3     3,4,5-Trimethylphenyl                                         628 CH.sub.3     Pentamethylphenyl                                             629 CH.sub.3     2-Ethylphenyl                                                 630 CH.sub.3     3-Ethylphenyl                                                 631 CH.sub.3     4-Ethylphenyl                                                 632 CH.sub.3     3,5-Diethylphenyl                                             633 CH.sub.3     2-n-Propylphenyl                                              634 CH.sub.3     3-n-Propylphenyl                                              635 CH.sub.3     4-n-Propylphenyl                                              636 CH.sub.3     2-iso-Propylphenyl                                            637 CH.sub.3     3-iso-Propylphenyl                                            638 CH.sub.3     4-iso-Propylphenyl                                            639 CH.sub.3     2,4-Di-iso-Propylphenyl                                       640 CH.sub.3     3,5-Di-iso-Propylphenyl                                       641 CH.sub.3     4-n-Butylphenyl                                               642 CH.sub.3     4-sec.-Butylphenyl                                            643 CH.sub.3     4-iso-Butylphenyl                                             644 CH.sub.3     4-tert.-Butylphenyl                                           645 CH.sub.3     3-tert.-Butylphenyl                                           646 CH.sub.3     2-tert.-Butylphenyl                                           647 CH.sub.3     2,4-Di-tert.-Butylphenyl                                      648 CH.sub.3     3,5-Di-tert.-Butylphenyl                                      649 CH.sub.3     4-n-Hexylphenyl                                               650 CH.sub.3     4-n-Dodecylphenyl                                             651 CH.sub.3     2-Methyl-4-tert.-Butylphenyl                                  652 CH.sub.3     2-Methyl-6-tert.-Butylphenyl                                  653 CH.sub.3     2-Methyl-4-iso-Propylphenyl                                   654 CH.sub.3     2-Methyl-4-Cyclohexylphenyl                                   655 CH.sub.3     2-Methyl-4-Phenylphenyl                                       656 CH.sub.3     2-Methyl-4-Benzylphenyl                                       657 CH.sub.3     2-Methyl-4-Phenoxyphenyl                                      658 CH.sub.3     2-Methyl-4-Benzyloxyphenyl                                    659 CH.sub.3     2-Methyl-3-Chlorophenyl                                       660 CH.sub.3     2-Methyl-4-Chlorophenyl                                       661 CH.sub.3     2-Methyl-5-Chlorophenyl                                       662 CH.sub.3     2-Methyl-6-Chlorophenyl                                       663 CH.sub.3     2-Methyl-4-Fluorophenyl                                       664 CH.sub.3     2-Methyl-3-Bromophenyl                                        665 CH.sub.3     2-Methyl-4-Bromophenyl                                        666 CH.sub.3     2-Methyl-3-Methoxyphenyl                                      667 CH.sub.3     2-Methyl-4-Methoxyphenyl                                      668 CH.sub.3     2-Methyl-5-Methoxyphenyl                                      669 CH.sub.3     2-Methyl-6-Methoxyphenyl                                      670 CH.sub.3     2-Methyl-4-iso-Propoxyphenyl                                  671 CH.sub.3     2-Methyl-2,5-Dimethoxyphenyl                                  672 CH.sub.3     2-Methoxyphenyl                                               673 CH.sub.3     3-Methoxyphenyl    oil; IR (film): 1708, 1634, 1285,                                              1256, 1129, 1111                           674 CH.sub.3     4-Methoxyphenyl    oil; IR (film): 1708, 1253, 1129           675 CH.sub.3     2,3-Dimethoxyphenyl                                           676 CH.sub.3     2,4-Dimethoxyphenyl                                           677 CH.sub.3     2,5-Dimethoxyphenyl                                           678 CH.sub.3     2,6-Dimethoxyphenyl                                           679 CH.sub.3     3,4-Dimethoxyphenyl                                           680 CH.sub.3     3,5-Dimethoxyphenyl                                           681 CH.sub.3     3,6-Dimethoxyphenyl                                           682 CH.sub.3     2,3,4-Trimethoxyphenyl                                        683 CH.sub.3     2,3,5-Trimethoxyphenyl                                        684 CH.sub.3     2,3,6-Trimethoxyphenyl                                        685 CH.sub.3     2,4,5-Trimethoxyphenyl                                        686 CH.sub.3     2,4,6-Trimethoxyphenyl                                        687 CH.sub.3     3,4,5-Trimethoxyphenyl                                        688 CH.sub.3     2-Ethoxyphenyl                                                689 CH.sub.3     3-Ethoxyphenyl                                                690 CH.sub.3     4-Ethoxyphenyl                                                691 CH.sub.3     2-iso-Propoxyphenyl                                           692 CH.sub.3     3-iso-Propoxyphenyl                                           693 CH.sub.3     4-iso-Propoxyphenyl                                           694 CH.sub.3     3-tert.-Butoxyphenyl                                          695 CH.sub.3     4-tert.-Butoxyphenyl                                          696 CH.sub.3     2-Trifluoromethoxyphenyl                                      697 CH.sub.3     3-Trifluoromethoxyphenyl                                      698 CH.sub.3     4-Trifluoromethoxyphenyl                                      699 CH.sub.3     3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                       700 CH.sub.3     4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                       701 CH.sub.3     2-Chloromethylphenyl                                          702 CH.sub.3     3-Chloromethylphenyl                                          703 CH.sub.3     4-Chloromethylphenyl                                          704 CH.sub.3     2-Trifluoromethylphenyl                                                                           oil; IR (film): 1705, 1634, 1313,                                              1130, 1107, 767                            705 CH.sub.3     3-Trifluoromethylphenyl                                                                           oil; IR (film): 1710, 1635, 1276,                                              1128                                       706 CH.sub.3     4-Trifluoromethylphenyl                                                                           m.p.: 104-5° C.;                                                        IR (KBr): 1697, 1628, 1323, 1123           707 CH.sub.3     2-(Methoxyiminomethyl)phenyl                                  708 CH.sub.3     3-(Methoxyiminomethyl)phenyl                                  709 CH.sub.3     4-(Methoxyiminomethyl)phenyl                                  710 CH.sub.3     2-(Ethoxyiminomethyl)phenyl                                   711 CH.sub.3     3-(Ethoxyiminomethyl)phenyl                                   712 CH.sub.3     4-(Ethoxyiminomethyl)phenyl                                   713 CH.sub.3     2-(n-Propoxyiminomethyl)phenyl                                714 CH.sub.3     3-(n-Propoxyiminomethyl)phenyl                                715 CH.sub.3     4-(n-Propoxyiminomethyl)phenyl                                716 CH.sub.3     2-(iso-Propoxyiminomethyl)phenyl                              717 CH.sub.3     3-(iso-Propoxyiminomethyl)phenyl                              718 CH.sub.3     4-(iso-Propoxyiminomethyl)phenyl                              719 CH.sub.3     2-(n-Butoxyiminomethyl)phenyl                                 720 CH.sub.3     3-(n-Butoxyiminomethyl)phenyl                                 721 CH.sub.3     4-(n-Butoxyiminomethyl)phenyl                                 722 CH.sub.3     2-(iso-Butoxyiminomethyl)phenyl                               723 CH.sub.3     3-(iso-Butoxyiminomethyl)phenyl                               724 CH.sub.3     4-(iso-Butoxyiminomethyl)phenyl                               725 CH.sub.3     2-(tert.-Butoxyiminomethyl)phenyl                             726 CH.sub.3     3-(tert.-Butoxyiminomethyl)phenyl                             727 CH.sub.3     4-(tert.-Butoxyiminomethyl)phenyl                             728 CH.sub.3     2-(n-Pentoxyiminomethyl)phenyl                                729 CH.sub.3     3-(n-Pentoxyiminomethyl)phenyl                                730 CH.sub.3     4-(n-Pentoxyiminomethyl)phenyl                                731 CH.sub.3     2-(n-Hexoxyiminomethyl)phenyl                                 732 CH.sub.3     3-(n-Hexoxyiminomethyl)phenyl                                 733 CH.sub.3     4-(n-Hexoxyiminomethyl)phenyl                                 734 CH.sub.3     2-(Allyloxyiminomethyl)phenyl                                 735 CH.sub.3     3-(Allyloxyiminomethyl)phenyl                                 736 CH.sub.3     4-(Allyloxyiminomethyl)phenyl                                 737 CH.sub.3     2-(Benzyloxyiminomethyl)phenyl                                738 CH.sub.3     3-(Benzyloxyiminomethyl)phenyl                                739 CH.sub.3     4-(Benzyloxyiminomethyl)phenyl                                740 CH.sub.3     2-(Methoxyimino-1'-ethyl)phenyl                               741 CH.sub.3     3-(Methoxyimino-1'-ethyl)phenyl                               742 CH.sub.3     4-(Methoxyimino-1'-ethyl)phenyl                               743 CH.sub.3     2-(Ethoxyimino-1'-ethyl)phenyl                                744 CH.sub.3     3-(Ethoxyimino-1'-ethyl)phenyl                                745 CH.sub.3     4-(Ethoxyimino-1'-ethyl)phenyl                                746 CH.sub.3     2-(n-Propoxyimino-1'-ethyl)phenyl                             747 CH.sub.3     3-(n-Propoxyimino-1'-ethyl)phenyl                             748 CH.sub.3     4-(n-Propoxyimino-1'-ethyl)phenyl                             749 CH.sub.3     2-(n-Butoxyamino-1'-ethyl)phenyl                              750 CH.sub.3     3-(n-Butoxyamino-1'-ethyl)phenyl                              751 CH.sub.3     4-(n-Butoxyamino-1'-ethyl)phenyl                              752 CH.sub.3     2-(n-Pentoxyimino-1'-ethyl)phenyl                             753 CH.sub.3     3-(n-Pentoxyimino-1'-ethyl)phenyl                             754 CH.sub.3     4-(n-Pentoxyimino-1'-ethyl)phenyl                             755 CH.sub.3     2-(n-Hexoxyimino-1'-ethyl)phenyl                              756 CH.sub.3     3-(n-Hexoxyimino-1'-ethyl)phenyl                              757 CH.sub.3     4-(n-Hexoxyimino-1'-ethyl)phenyl                              758 CH.sub.3     2-(Allyloxyimino-1'-ethyl)phenyl                              759 CH.sub.3     3-(Allyloxyimino-1'-ethyl)phenyl                              760 CH.sub.3     4-(Allyloxyimino-1'-ethyl)phenyl                              761 CH.sub.3     2-(Benzyloxyimino-1'-ethyl)phenyl                             762 CH.sub.3     3-(Benzyloxyimino-1'-ethyl)phenyl                             763 CH.sub.3     4-(Benzyloxyimino-1'-ethyl)phenyl                             764 CH.sub.3     2-Phenylphenyl                                                765 CH.sub.3     3-Phenylphenyl                                                766 CH.sub.3     4-Phenylphenyl                                                767 CH.sub.3     2-Phenoxyphenyl                                               768 CH.sub.3     3-Phenoxyphenyl                                               769 CH.sub.3     4-Phenoxyphenyl    oil; IR (film): 1708, 1489, 1240,                                              1129                                       770 CH.sub.3     2-Benzyloxyphenyl                                             771 CH.sub.3     3-Benzyloxyphenyl                                             772 CH.sub.3     4-Benzyloxyphenyl                                             773 CH.sub.3     4-(Imidazol-1'-yl)phenyl                                      774 CH.sub.3     4-(Piperazin-1'-yl)phenyl                                     775 CH.sub.3     4-(Morpholin-1'-yl)phenyl                                     776 CH.sub.3     4-(Piperidin-1'-yl)phenyl                                     777 CH.sub.3     4-(Pyridyl-2'-oxy)phenyl                                      778 CH.sub.3     2-Cyclopropylphenyl                                           779 CH.sub.3     3-Cyclopropylphenyl                                           780 CH.sub.3     4-Cyclopropylphenyl                                           781 CH.sub.3     3-Cyclohexylphenyl                                            782 CH.sub.3     4-Cyclohexylphenyl                                            783 CH.sub.3     4-Oxiranylphenyl                                              784 CH.sub.3     4-(1',3'-Dioxan-2'-yl)phenyl                                  785 CH.sub.3     4-(Tetrahydropyran-2-yloxy)phenyl                             786 CH.sub.3     1-Naphthyl                                                    787 CH.sub.3     2-Naphthyl                                                    788 CH.sub.3     9-Anthryl                                                     789 CH.sub.3     1-Naphthoxy                                                   790 CH.sub.3     2-Naphthoxy                                                   791 CH.sub.3     9-Anthroxy                                                    792 CH.sub.3     Phenoxy                                                       793 CH.sub.3     2-Chlorophenoxy                                               794 CH.sub.3     3-Chlorophenoxy                                               795 CH.sub.3     4-Chlorophenoxy                                               796 CH.sub.3     4-Methylphenoxy                                               797 CH.sub.3     4-tert.-Butylphenoxy                                          798 CH.sub.3     4-Methoxyphenoxy                                              799 CH.sub.3     4-Ethoxyphenoxy                                               800 CH.sub.3     4-tert.-Butoxyphenoxy                                         801 CH.sub.3     Phenylthio                                                    862 CH.sub.3     2-Chlorophenylthio                                            803 CH.sub.3     4-Chlorophenylthio                                            804 CH.sub.3     Benzyl                                                        805 CH.sub.3     2-Methylbenzyl                                                806 CH.sub.3     3-Methylbenzyl                                                807 CH.sub.3     4-Methylbenyzl                                                808 CH.sub.3     4-tert.-Butylbenzyl                                           809 CH.sub.3     2-Chlorobenzyl                                                810 CH.sub.3     3-Chlorobenzyl                                                811 CH.sub.3     4-Chlorobenzyl                                                812 CH.sub.3     2,4-Dichlorobenzyl                                            813 CH.sub.3     2,6-Dichlorobenzyl                                            814 CH.sub.3     2,4,6-Trichlorobenzyl                                         815 CH.sub.3     2-Trifluoromethylbenzyl                                       816 CH.sub.3     3-Trifluoromethylbenzyl                                       817 CH.sub.3     4-Trifluoromethylbenzyl                                       818 CH.sub.3     2-Methoxybenzyl                                               819 CH.sub.3     4-Methoxybenzyl                                               820 CH.sub.3     4-tert.-Butoxybenzyl                                          821 CH.sub.3     4-Phenoxybenzyl                                               822 CH.sub.3     1-Phenethyl                                                   823 CH.sub.3     2-Phenethyl                                                   824 CH.sub.3     1-Phenylpropyl                                                825 CH.sub.3     2-Phenylpropyl                                                826 CH.sub.3     3-Phenylpropyl                                                827 CH.sub.3     2-Methyl-2-phenylpropyl                                       828 CH.sub.3     2-Methyl-3-phenylpropyl                                       829 CH.sub.3     4-Phenylbutyl                                                 830 CH.sub.3     2-Phenyl-1-ethenyl                                            831 CH.sub.3     1-Phenyl-l-ethenyl                                            832 CH.sub.3     1-Phenyl-1-propenyl                                           833 CH.sub.3     1-Phenyl-1-propen-2-yl                                        834 CH.sub.3     2,2-Diphenylethenyl                                           835 CH.sub.3     Phenoxymethyl                                                 836 CH.sub.3     2-Pyridyl                                                     837 CH.sub.3     3-Pyridyl                                                     838 CH.sub.3     4-Pyridyl                                                     839 CH.sub.3     2,6-Pyrimidinyl                                               840 CH.sub.3     1,5-Pyrimidinyl                                               841 CH.sub.3     2-Thienyl                                                     842 CH.sub.3     3-Thienyl                                                     843 CH.sub.3     2-Furyl                                                       844 CH.sub.3     3-Furyl                                                       845 CH.sub.3     1-Pyrrolyl                                                    846 CH.sub.3     1-Imidazolyl                                                  847 CH.sub.3     1,2,4-Triazolyl                                               848 CH.sub.3     1,3,4-Triazolyl                                               849 CH.sub.3     4-Thiazolyl                                                   850 CH.sub.3     2-Benzothiazolyl                                              851 CH.sub.3     2-Pyridyloxy                                                  852 CH.sub.3     2-Pyrimidinyloxy                                              853 CH.sub.3     2-Pyridylthio                                                 854 CH.sub.3     2-Pyrimidinylthio                                             855 CH.sub.3     2-Benzothiazolylthio                                          856 CH.sub.3     Phenylthiomethyl                                              857 CH.sub.3     2-Pyridylmethyl                                               858 CH.sub.3     3-Pyridylmethyl                                               859 CH.sub.3     Furfuryloxy                                                   860 CH.sub.3     Thienylmethoxy                                                861 CH.sub.3     3-Isoxazolylmethoxy                                           862 CH.sub.3     2-Oxazolylmethoxy                                             863 CH.sub.3     2-Pyridylmethoxy                                              864 CH.sub.3     2'-Furyl-2-ethenyl                                            865 CH.sub.3     2'-Thienyl-2-ethenyl                                          866 CH.sub.3     3'-Pyridyl-2-ethenyl                                          867 CH.sub.3     Oxiranyl                                                      868 CH.sub.3     1-Aziridinyl                                                  869 CH.sub.3     1-Azetidinyl                                                  870 CH.sub.3     1-Pyrrolidinyl                                                871 CH.sub.3     2-Tetrahydrofuryl                                             872 CH.sub.3     2-Tetrahydropyranyl                                           873 CH.sub.3     3-Tetrahydropyranyl                                           874 CH.sub.3     1-Piperidinyl                                                 875 CH.sub.3     1-Morpholinyl                                                 076 CH.sub.3     1-Piperazinyl                                                 877 CH.sub.3     1,3-Dioxan-2-yl                                               878 CH.sub.3     3-Tetrahydrothiopyranyl                                       879 CH.sub.3     2-Dihydropyranyloxy                                           880 CH.sub.3     2-Tetrahydropyranyloxy                                        881 CH.sub.3     CF.sub.3                                                      882 CH.sub.3     2-Fluoroethyl                                                 883 CH.sub.3     2,2,2-Trifluoroethyl                                          884 CH.sub.3     Pentafluoroethyl                                              885 CH.sub.3     Chloromethyl                                                  886 CH.sub.3     Dichloromethyl                                                887 CH.sub.3     Trichloromethyl                                               888 CH.sub.3     2-Chloroethyl                                                 889 CH.sub.3     2,2,2-Trichloroethyl                                          890 CH.sub.3     Pentachloroethyl                                              891 CH.sub.3     Cyclopropyl                                                   892 CH.sub.3     Cyclobutyl                                                    893 CH.sub.3     Cyclopentyl                                                   894 CH.sub.3     Cyclohexyl                                                    895 CH.sub.3     1-Methylcyclopropyl                                           896 CH.sub.3     2,2-Dimethylcyclopropyl                                       897 CH.sub.3     1-Methylcyclohexyl                                            898 CH.sub.3     2,2-Difluorocyclopropyl                                       899 CH.sub.3     2,2-Dichlorocyclopropyl                                       900 CH.sub.3     2,2-Dibromocyclopropyl                                        901 CH.sub.3     2,2-Dichloro-3-methylcyclopropyl                              902 CH.sub.3     2,2,3,3-Tetrafluorocyclobutyl                                 903 CH.sub.3     Ethenyl                                                       904 CH.sub.3     1-Propenyl                                                    905 CH.sub.3     2-Methyl-1-propenyl                                           906 CH.sub.3     4-Methylpent-3-en-1-yl                                        907 CH.sub.3     2-Propenyl                                                    908 CH.sub.3     2-Butenyl                                                     909 CH.sub.3     1-Methyl-2-propenyl                                           910 CH.sub.3     3-Methyl-2-butenyl                                            911 CH.sub.3     2,2-Difluoroethenyl                                           912 CH.sub.3     2,2-Dichloroethenyl                                           913 CH.sub.3     3,3,3-Trifluoropropenyl                                       914 CH.sub.3     3,3,3-Trichloropropenyl                                       915 CH.sub.3     3-Chloro-2-propenyl                                           916 CH.sub.3     Cyclopent-1-enyl                                              917 CH.sub.3     Cyclopentadienyl                                              918 CH.sub.3     Cyclohex-1-enyl                                               919 CH.sub.3     Pentafluorocyclopentadienyl                                   920 CH.sub.3     Pentachlorocyclopentadienyl                                   921 Phenyl       Phenyl                                                        922 Phenyl       2-Fluorophenyl                                                923 Phenyl       4-Fluorophenyl                                                924 Phenyl       2-Chlorophenyl                                                925 Phenyl       3-Chlorophenyl                                                926 Phenyl       4-Chlorophenyl                                                927 Phenyl       3,4-Dichlorophenyl                                            928 Phenyl       4-Nitrophenyl                                                 929 Phenyl       2-CF.sub.3 -Phenyl                                            930 Phenyl       3-CF.sub.3 -Phenyl                                            931 Phenyl       4-CF.sub.3 -Phenyl                                            932 Phenyl       2-Methylphenyl                                                933 Phenyl       3-Methylphenyl                                                934 Phenyl       4-Methylphenyl                                                935 Phenyl       2,4-Dimethylphenyl                                            936 Phenyl       4-tert.-Butylphenyl                                           937 Phenyl       4-Methoxyphenyl                                               938 4-Fluorophenyl                                                                              4-Fluorophenyl                                                939 2-Fluorophenyl                                                                              4-Fluorophenyl                                                940 2-Chlorophenyl                                                                              4-Fluorophenyl                                                941 2-Chlorophenyl                                                                              2-Chlorophenyl                                                942 3-Chlorophenyl                                                                              3-Chlorophenyl                                                943 4-Chlorophenyl                                                                              4-Chlorophenyl                                                944 2-Chlorophenyl                                                                              4-Chlorophenyl                                                945 4-Methoxyphenyl                                                                             4-Methoxyphenyl                                               946 4-Dimethylaminophenyl                                                                       4-Dimethylaminophenyl                                         947 Phenyl       Naphthyl                                                      948 Ethyl        Ethyl                                                         949 Ethyl        n-Propyl                                                      950 Ethyl        iso-Propyl                                                    951 Ethyl        n-Butyl                                                       952 Ethyl        iso-Butyl                                                     953 Ethyl        2-Methyl-butyl                                                954 Ethyl        Benzyl                                                        955 n-Propyl     n-Propyl                                                      956 iso-Propyl   iso-Propyl                                                    957 n-Butyl      n-Butyl                                                       958 iso-Butyl    iso-Butyl                                                     959 tert.-Butyl  tert.-Butyl                                                   960 Benzyl       Benzyl                                                        961 Pentachloroethyl                                                                            Pentachloroethyl                                              962 n-Hexyl      n-Hexyl                                                       963 Ethoxycarbonyl                                                                              Ethoxycarbonyl                                                964 Phenyl       Benzoyl                                                       965 Ethyl        Phenyl                                                        966 n-Butyl      Phenyl                                                        967 Styryl       Styryl                                                        968 2-Pyridyl    2-Pyridyl                                                     969 3-Pyridyl    3-Pyridyl                                                     970 CH.sub.3     3,5-Dibenzyloxyphenyl                                                                             IR (film): 1707, 1581, 1256, 1157,                                             1129                                       __________________________________________________________________________

                  TABLE II                                                         ______________________________________                                          ##STR20##                                                                     No.  R.sup.3    R.sup.4         Data                                           ______________________________________                                         1    Cl         Phenyl                                                         2    Cl         Cyano                                                          3    Cl         Ethoxycarbonyl                                                 4    Cl         Cyclopropyl                                                    5    CF.sub.3   CF.sub.3                                                       6    CF.sub.3   Phenyl                                                         7    CCl.sub.3  CCl.sub.3                                                      8    CCl.sub.3  Phenyl                                                         9    CH.sub.2 Cl                                                                               Phenyl                                                         10   CF.sub.2 CF.sub.3                                                                         Phenyl                                                         11   CF.sub.2 Cl                                                                               Phenyl                                                         12   CHCl.sub.2 Phenyl                                                         13   Cyclo-     Cyclopropyl                                                         propyl                                                                    14   Cyclo-     Phenyl          oil; IR (film):                                     propyl                     1437 1321, 1219,                                                               1045, 983, 766                                 15   Cyclo-     4-Fluorophenyl  oil; IR (film):                                     propyl                     1508, 1321, 1222,                                                              1046, 985, 839                                 16   Cyclo-     4-Chlorophenyl  oil; IR (film):                                     propyl                     1489, 1321, 1218,                                                              1090, 1046, 829                                17   Cyclo-     4-Methoxyphenyl oil; IR (film):                                     propyl                     1300, 1250, 1218,                                                              983, 833                                       18   Cyclo-     4-Ethoxyphenyl                                                      propyl                                                                    19   Cyclo-     4-Phenoxyphenyl                                                     propyl                                                                    20   Cyclo-     Pentachlorophenyl                                                   propyl                                                                    21   Cyclo-     Pentafluorophenyl                                                   propyl                                                                    22   Cyclo-     Phenyl                                                              pentyl                                                                    23   Cyclo-     Phenyl                                                              hexyl                                                                     24   Phenyl     2,2-Dichloro-1-methyl-                                                         cyclopropyl                                                    25   Phenyl     2,2-Difluorocyclo-                                                             propyl                                                         26   Phenyl     2,2-Dichlorocyclo-                                                             propyl                                                         27   Phenyl     2,2-Dibromocyclo-                                                              propyl                                                         28   Phenyl     2,2,3,3-Tetrafluoro-                                                           cyclobutyl                                                     29   Phenyl     2,2-Dimethylcyclo-                                                             propyl                                                         30   Phenyl     1-Methylcyclohexyl                                             31   CN         Methoxymethyl                                                  32   CN         Ethoxymethyl                                                   33   CN         n-Propoxymethyl                                                34   CN         iso-Propoxymethyl                                              35   CN         tert.-Butoxymethyl                                             36   CN         2-Methoxyprop-2-yl                                                                             m.p.: 83° C.;                                                           IR (KBr): 1437,                                                                1223, 1206, 1069,                                                              1006                                           37   CN         2-Ethoxyprop-2-yl                                                                              oil; IR (film):                                                                1439, 3122, 1221,                                                              1202, 1048                                     38   CN         2-n-Propoxyprop-2-yl                                                                           oil; IR (film):                                                                1438, 1322, 1221,                                                              1203, 1048                                     39   CN         2-iso-Propoxyprop-2-yl                                                                         m.p.: 74-5° C.                                                          IR (KBr): 1302,                                                                1231, 1169, 1108,                                                              1079, 997, 757                                 40   CN         2-tert.-Butoxyprop-2-yl                                        41   CN         Methylthiomethyl                                               42   CN         tert.-Butylthiomethyl                                          43   CN         2-Methylthioprop-2-yl                                                                          m.p.: 107° C.;                                                          IR (KBr): 1434,                                                                1297, 1126, 1066,                                                              1010, 769                                      44   CN         2-iso-Propylthioprop-                                                                          oil; IR (film):                                                2-yl            1438, 1366, 1321,                                                              1221, 1202                                     45   CN         2-tert.-Butylthioprop-                                                         2-yl                                                           46   CN         Methyl                                                         47   CN         Ethyl                                                          48   CN         n-Propyl                                                       49   CN         iso-Propyl      oil; IR (film):                                                                1439, 1321, 1222,                                                              1012, 767                                      50   CN         n-Butyl                                                        51   CN         iso-Butyl                                                      52   CN         sec.-Butyl                                                     53   CN         tert.-Butyl                                                    54   CN         n-Hexyl                                                        55   CN         n-Decyl                                                        56   CN         Cyclopropyl     m.p.: 74-75° C.;                                                        IR (KBr): 1433,                                                                1223, 1043, 763                                57   CN         Cyclohexyl                                                     58   CN         Phenylthiomethyl                                               59   CN         2-Phenylthiomethyl                                             60   CN         2-(2'-Chlorophenyl-                                                            thio)prop-2-yl                                                 61   CN         Ethynyl                                                        62   CN         1-Propynyl                                                     63   CN         Methoxy                                                        64   CN         Ethoxy                                                         65   CN         n-Propoxy                                                      66   CN         lso-Propoxy                                                    67   CN         n-Butoxy                                                       68   CN         iso-Butoxy                                                     69   CN         sec.-Butoxy                                                    70   CN         tert.-Butoxy                                                   71   CN         Methylthio                                                     72   CN         Ethylthio                                                      73   CN         n-Propylthio                                                   74   CN         iso-Propylthio                                                 75   CN         n-Butylthio                                                    76   CN         iso-Butylthio                                                  77   CN         sec.-Butylthio                                                 78   CN         tert.-Butylthio                                                79   CN         Benzylthio                                                     80   CN         Trifluoromethoxy                                               81   CN         Cyano                                                          82   CN         Amino                                                          83   CN         Methylamino                                                    84   CN         Dimethylamino                                                  85   CN         Ethylamino                                                     86   CN         Diethylamino                                                   87   CN         Di-n-Propylamino                                               88   CN         Di-iso-Propylamino                                             89   CN         Di-n-Butylamino                                                90   CN         Di-iso-Butylamino                                              91   CN         Acetyl                                                         92   CN         Propion-1-yl                                                   93   CN         Butyr-1-yl                                                     94   CN         iso-Butyr-1-yl                                                 95   CN         Pivaloyl                                                       96   CN         Benzoyl                                                        97   CN         4-Chlorobenzoyl                                                98   CN         Benzylcarbonyl                                                 99   CN         Methoxycarbonyl                                                100  CN         Ethoxycarbonyl                                                 101  CN         n-Propoxycarbonyl                                              102  CN         iso-Propoxycarbonyl                                            103  CN         n-Butoxycarbonyl                                               104  CN         iso-Butoxycarbonyl                                             105  CN         sec.-Butoxycarbonyl                                            106  CN         tert.-Butoxycarbonyl                                           107  CN         n-Hexoxycarbonyl                                               108  CN         Phenoxycarbonyl                                                109  CN         4-Chlorophenoxy-                                                               carbonyl                                                       110  CN         Benzyloxycarbonyl                                              111  CN         Aminocarbonyl                                                  112  CN         Dimethylamino-                                                                 carbonyl                                                       113  CN         Diethylaminocarbonyl                                           114  CN         Di-iso-Propylamino-                                                            carbonyl                                                       115  CN         Phenylaminocarbonyl                                            116  CN         N-Methyl-N-Phenyl-                                                             aminocarbonyl                                                  117  CN         Phenyl          m.p.: 99-100° C.;                                                       IR (KBr): 1436,                                                                1215, 1208, 1097,                                                              1026, 944, 766,                                                                690                                            118  CN         2-Fluorophenyl                                                 119  CN         3-Fluorophenyl                                                 120  CN         4-Fluorophenyl                                                 121  CN         Pentafluorophenyl                                              122  CN         2-Chlorophenyl                                                 123  CN         3-Chlorophenyl                                                 124  CN         4-Chlorophenyl                                                 125  CN         Pentachlorophenyl                                              126  CN         2,3-Dichlorophenyl                                             127  CN         2,4-Dichlorophenyl                                             128  CN         2,5-Dichlorophenyl                                             129  CN         2,6-Dichlorophenyl                                             130  CN         3,4-Dichlorophenyl                                             131  CN         3,5-Dichlorophenyl                                             132  CN         2,3,4-Trichlorophenyl                                          133  CN         2,3,5-Trichlorophenyl                                          134  CN         2,3,6-Trichlorophenyl                                          135  CN         2,4,5-Trichlorophenyl                                          136  CN         2,4,6-Trichlorophenyl                                          137  CN         3,4,5-Trichlorophenyl                                          138  CN         2,3,4,6-Tetrachloro-                                                           phenyl                                                         139  CN         2,3,5-6-Tetrachloro-                                                           phenyl                                                         140  CN         2-Bromophenyl                                                  141  CN         3-Bromophenyl                                                  142  CN         4-Bromophenyl                                                  143  CN         2,4-Dibromophenyl                                              144  CN         3-Bromo-4-fluoro-                                                              phenyl                                                         145  CN         3-Bromo-4-methoxy-                                                             phenyl                                                         146  CN         2-Iodophenyl                                                   147  CN         3-Iodophenyl                                                   148  CN         4-Iodophenyl                                                   149  CN         2-Chloro-4-fluorophenyl                                        150  CN         2-Chloro-5-fluorophenyl                                        151  CN         2-Chloro-6-fluorophenyl                                        152  CN         2-Chloro-4-bromophenyl                                         153  CN         2-Bromo-4-chlorophenyl                                         154  CN         2-Bromo-4-fluorophenyl                                         155  CN         3-Bromo-4-chlorophenyl                                         156  CN         3-Chloro-4-fluorophenyl                                        157  CN         3-Fluoro-4-chlorophenyl                                        158  CN         2-Cyanophenyl                                                  159  CN         3-Cyanophenyl                                                  160  CN         4-Cyanophenyl                                                  161  CN         2-Nitrophenyl                                                  162  CN         3-Nitrophenyl                                                  163  CN         4-Nitrophenyl                                                  164  CN         2-Methylphenyl                                                 165  CN         3-Methylphenyl                                                 166  CN         4-Methylphenyl                                                 167  CN         2,4-Dimethylphenyl                                             168  CN         2,6-Dimethylphenyl                                             169  CN         3,4-Dimethylphenyl                                             170  CN         3,5-Dimethylphenyl                                             171  CN         2,3,4-Trimethylphenyl                                          172  CN         2,3,5-Trimethylphenyl                                          173  CN         2,3,6-Trimethylphenyl                                          174  CN         2,4,5-Trimethylphenyl                                          175  CN         2,4,6-Trimethylphenyl                                          176  CN         3,4,5-Trimethylphenyl                                          177  CN         Pentamethylphenyl                                              178  CN         2-Ethylphenyl                                                  179  CN         3-Ethylphenyl                                                  180  CN         4-Ethylphenyl                                                  181  CN         3,5-Diethylphenyl                                              182  CN         2-n-Propylphenyl                                               183  CN         3-n-Propylphenyl                                               184  CN         4-n-Propylphenyl                                               185  CN         2-iso-Propylphenyl                                             186  CN         3-iso-Propylphenyl                                             187  CN         4-iso-Propylphenyl                                             188  CN         2,4-Di-lso-Propyl-                                                             phenyl                                                         189  CN         3,5-Di-iso-Propyl-                                                             phenyl                                                         190  CN         4-n-Butylphenyl                                                191  CN         4-sec.-Butylphenyl                                             192  CN         4-iso-Butylphenyl                                              193  CN         4-tert.-Butylphenyl                                            194  CN         3-tert.-Butylphenyl                                            195  CN         2-tert.-Butylphenyl                                            196  CN         2,4-Di-tert.-Butylphenyl                                       197  CN         3,5-Di-tert.-Butylphenyl                                       198  CN         4-n-Hexylphenyl                                                199  CN         4-n-Dodecylphenyl                                              200  CN         2-Methyl-4-tert.-Butyl-                                                        phenyl                                                         201  CN         2-Methyl-6-tert.-Butyl-                                                        phenyl                                                         202  CN         2-Methyl-4-iso-Propyl-                                                         phenyl                                                         203  CN         2-Methyl-4-Cyclo-                                                              hexylphenyl                                                    204  CN         2-Methyl-4-Phenyl-                                                             phenyl                                                         205  CN         2-methyl-4-Benzyl-                                                             phenyl                                                         206  CN         2-Methyl-4-Phenoxy-                                                            phenyl                                                         207  CN         2-Methyl-4-Benzyloxy-                                                          phenyl                                                         208  CN         2-Methyl-3-Chloro-                                                             phenyl                                                         209  CN         2-Methyl-4-Chloro-                                                             phenyl                                                         210  CN         2-Methyl-5-Chloro-                                                             phenyl                                                         211  CN         2-Methyl-6-Chloro-                                                             phenyl                                                         212  CN         2-Methyl-4-Fluoro-                                                             phenyl                                                         213  CN         2-methyl-3-Bromo-                                                              phenyl                                                         214  CN         2-Methyl-4-Bromo-                                                              phenyl                                                         215  CN         2-methyl-3-Methoxy-                                                            phenyl                                                         216  CN         2-Methyl-4-Methoxy-                                                            phenyl                                                         217  CN         2-Methyl-5-Methoxy-                                                            phenyl                                                         218  CN         2-Methyl-6-Methoxy-                                                            phenyl                                                         219  CN         2-Methyl-4-iso-                                                                Propoxyphenyl                                                  220  CN         2-Methyl-2,5-                                                                  Dimethoxyphenyl                                                221  CN         2-Methoxyphenyl                                                222  CN         3-Methoxyphenyl                                                223  CN         4-Methoxyphenyl                                                224  CN         2,3-Dimethoxyphenyl                                            225  CN         2,4-Dimethoxyphenyl                                            226  CN         2,5-Dimethoxyphenyl                                            227  CN         2,6-Dimethoxyphenyl                                            228  CN         3,4-Dimethoxyphenyl                                            229  CN         3,5-Dimethoxyphenyl                                            230  CN         3,6-Dimethoxyphenyl                                            231  CN         2,3,4-Trimethoxyphenyl                                         232  CN         2,3,5-Trimethoxyphenyl                                         233  CN         2,3,6-Trimethoxyphenyl                                         234  CN         2,4,5-Trimethoxyphenyl                                         235  CN         2,4,6-Trimethoxyphenyl                                         236  CN         3,4,5-Trimethoxyphenyl                                         237  CN         2-Ethoxyphenyl                                                 238  CN         3-Ethoxyphenyl                                                 239  CN         4-Ethoxyphenyl                                                 240  CN         2-iso-Propoxyphenyl                                            241  CN         3-iso-Propoxyphenyl                                            242  CN         4-iso-Propoxyphenyl                                            243  CN         3-tert.-Butoxyphenyl                                           244  CN         4-tert.-Butoxyphenyl                                           245  CN         2-Trifluoromethoxy-                                                            phenyl                                                         246  CN         3-Trifluoromethoxy-                                                            phenyl                                                         247  CN         4-Trifluoromethoxy-                                                            phenyl                                                         248  CN         3-(1',1',2',2'-Tetra-                                                          fluoro)ethoxyphenyl                                            249  CN         4-(1',1',2',2'-Tetra-                                                          fluoro)ethoxyphenyl                                            250  CN         2-Chloromethylphenyl                                           251  CN         3-Chloromethylphenyl                                           252  CN         4-Chloromethylphenyl                                           253  CN         2-Trifluoromethylphenyl                                        254  CN         3-Trifluoromethylphenyl                                        255  CN         4-Trifluoromethylphenyl                                        256  CN         2-(Methoxyimino-                                                               methyl)phenyl                                                  257  CN         3-(Methoxyimino-                                                               methyl)phenyl                                                  258  CN         4-(Methoxyimino-                                                               methyl)phenyl                                                  259  CN         2-(Ethoxyimino-                                                                methyl)phenyl                                                  260  CN         3-(Ethoxyimino-                                                                methyl)phenyl                                                  261  CN         4-(Ethoxyimino-                                                                methyl)phenyl                                                  262  CN         2-(n-Propoxyimino-                                                             methyl)phenyl                                                  263  CN         3-(n-Propoxyimino                                                              methyl)phenyl                                                  264  CN         4-(n-Propoxyimino-                                                             methyl)phenyl                                                  265  CN         2-(iso-Propoxyimino-                                                           methyl)phenyl                                                  266  CN         3-(iso-Propoxyimino-                                                           methyl)phenyl                                                  267  CN         4-(iso-Propoxyimino-                                                           methyl)phenyl                                                  268  CN         2-(n-Butoxyimino-                                                              methyl)phenyl                                                  269  CN         3-(n-Butoxyimino-                                                              methyl)phenyl                                                  270  CN         4-(n-Butoxyimino-                                                              methyl)phenyl                                                  271  CN         2-(iso-Butoxyimino-                                                            methyl)phenyl                                                  272  CN         3-(iso-Butoxyimino-                                                            methyl)phenyl                                                  273  CN         4-(iso-Butoxyimino-                                                            methyl)phenyl                                                  274  CN         2-(tert.-Butoxyimino-                                                          methyl)phenyl                                                  275  CN         3-(tert.-Butoxyimino-                                                          methyl)phenyl                                                  276  CN         4-(tert.-Butoxyimino-                                                          methyl)phenyl                                                  277  CN         2-(n-Pentoxyimino-                                                             methyl)phenyl                                                  278  CN         3-(n-Pentoxyimino-                                                             methyl)phenyl                                                  279  CN         4-(n-Pentoxyimino-                                                             methyl)phenyl                                                  280  CN         2-(n-Hexoxyimino-                                                              methyl)phenyl                                                  281  CN         3-(n-Hexoxyimino-                                                              methyl)phenyl                                                  282  CN         4-(n-Hexoxyimino-                                                              methyl)phenyl                                                  283  CH         2-(Allyloxyimino-                                                              methyl)phenyl                                                  284  CN         3-(Allyloxyimino-                                                              methyl)phenyl                                                  285  CN         4-(Allyloxyimino-                                                              methyl)phenyl                                                  286  CH         2-(Benzyloxyimino-                                                             methyl)phenyl                                                  287  CN         3-(Benzyloxyimino-                                                             methyl)phenyl                                                  288  CN         4-(Benzyloxyimino-                                                             methyl)phenyl                                                  289  CN         2-(Methoxyimino-1'-                                                            ethyl)phenyl                                                   290  CN         3-(Methoxyimino-1'-                                                            ethyl)phenyl                                                   291  CN         4-(Methoxyimino-1'-                                                            ethyl)phenyl                                                   292  CN         2-(Ethoxyimino-1'-                                                             ethyl)phenyl                                                   293  CN         3-(Ethoxyimino-1'-                                                             ethyl)phenyl                                                   294  CN         4-(Ethoxyimino-1'-                                                             ethyl)phenyl                                                   295  CN         2-(n-Propoxyimino-1'-                                                          ethyl)phenyl                                                   296  CN         3-(n-Propoxyimino-1'-                                                          ethyl)phenyl                                                   297  CN         4-(n-Propoxyimino-1'-                                                          ethyl)phenyl                                                   298  CN         2-(n-Butoxyamino-1'-                                                           ethyl)phenyl                                                   299  CN         3-(n-Butoxyamino-1'-                                                           ethyl)phenyl                                                   300  CN         4-(n-Butoxyamino-1'-                                                           ethyl)phenyl                                                   301  CN         2-(n-Pentoxyimino-1'-                                                          ethyl)phenyl                                                   302  CN         3-(n-Pentoxyimino-1'-                                                          ethyl)phenyl                                                   303  CN         4-(n-Pentoxyimino-1'-                                                          ethyl)phenyl                                                   304  CN         2-(n-Hexoxyimino-1'-                                                           ethyl)phenyl                                                   305  CN         3-(n-Hexoxyimino-1'-                                                           ethyl)phenyl                                                   306  CN         4-(n-Hexoxyimino-1'-                                                           ethyl)phenyl                                                   307  CN         2-(Allyloxyimino-1'-                                                           ethyl)phenyl                                                   308  CN         3-(Allyloxyimino-1'-                                                           ethyl)phenyl                                                   309  CN         4-(Allyloxyimino-1'-                                                           ethyl)phenyl                                                   310  CN         2-(Benzyloxyimino-1'-                                                          ethyl)phenyl                                                   311  CN         3-(Benzyloxyimino-1'-                                                          ethyl)phenyl                                                   312  CN         4-(Benzyloxyimino-1'-                                                          ethyl)phenyl                                                   313  CN         2-Phenylphenyl                                                 314  CN         3-Phenylphenyl                                                 315  CN         4-Phenylphenyl                                                 316  CN         2-Phenoxyphenyl                                                317  CN         3-Phenoxyphenyl                                                318  CN         4-Phenoxyphenyl                                                319  CN         2-Benzyloxyphenyl                                              320  CN         3-Benzyloxyphenyl                                              321  CN         4-Benzyloxyphenyl                                              322  CN         4-(imidazol-1'-                                                                yl)phenyl                                                      323  CN         4-(Piperazin-1'-                                                               yl)phenyl                                                      324  CN         4-(Morpholin-1'-                                                               yl)phenyl                                                      325  CN         4-(Piperidin-1'-                                                               yl)phenyl                                                      326  CN         4-(Pyridyl-2'-                                                                 oxy)phenyl                                                     327  CN         2-Cyclopropylphenyl                                            328  CN         3-Cyclopropylphenyl                                            329  CN         4-Cyclopropylphenyl                                            330  CN         3-Cyclohexylphenyl                                             331  CN         4-Cyclohexylphenyl                                             332  CN         4-Oxiranylphenyl                                               333  CN         4-(1',3'-Dioxan-2'-                                                            yl)phenyl                                                      334  CN         4-(Tetrahydropyran-2-                                                          yloxy)phenyl                                                   335  CN         1-Naphthyl                                                     336  CN         2-Naphthyl                                                     337  CN         9-Anthryl                                                      338  CN         1-Naphthoxy                                                    339  CN         2-Naphthoxy                                                    340  CN         9-Anthroxy                                                     341  CN         Phenoxy                                                        342  CN         2-Chlorophenoxy                                                343  CN         3-Chlorophenoxy                                                344  CN         4-Chlorophenoxy                                                345  CN         4-Methylphenoxy                                                346  CN         4-tert.-Butylphenoxy                                           347  CN         4-Methoxyphenoxy                                               348  CN         4-Ethoxyphenoxy                                                349  CN         4-tert.-Butoxyphenoxy                                          350  CN         Phenylthio                                                     351  CN         2-Chlorophenylthio                                             352  CN         4-Chlorophenylthio                                             353  CN         Benzyl                                                         354  CN         2-Methylbenzyl                                                 355  CN         3-Methylbenzyl                                                 356  CN         4-Methylbenzyl                                                 357  CN         4-tert.-Butylbenzyl                                            358  CN         2-Chlorobenzyl                                                 359  CN         3-Chlorobenzyl                                                 360  CN         4-Chlorobenzyl                                                 361  CN         2,4-Dichlorobenzyl                                             362  CN         2,6-Dichlorobenzyl                                             363  CN         2,4,6-Trichlorobenzyl                                          364  CN         2-Trifluoromethyl-                                                             benzyl                                                         365  CN         3-Trifluoromethyl-                                                             benzyl                                                         366  CN         4-Trifluoromethyl-                                                             benzyl                                                         367  CN         2-Methoxybenzyl                                                368  CN         4-Methoxybenzyl                                                369  CN         4-tert.-Butoxybenzyl                                           370  CN         4-Phenoxybenzyl                                                371  CN         1-Phenethyl                                                    372  CN         2-Phenethyl                                                    373  CN         1-Phenylpropyl                                                 374  CN         2-Phenylpropyl                                                 375  CN         3-Phenylpropyl                                                 376  CN         2-Methyl-2-phenyl-                                                             propyl                                                         377  CN         2-Methyl-3-phenyl-                                                             propyl                                                         378  CN         4-Phenylbutyl                                                  379  CN         2-Phenyl-1-ethenyl                                             380  CN         1-Phenyl-1-ethenyl                                             381  CN         1-Phenyl-1-propenyl                                            382  CN         1-Phenyl-1-propen-2-yl                                         383  CN         2,2-Diphenylethenyl                                            384  CN         Phenoxymethyl                                                  385  CN         2-Pyridyl                                                      386  CN         3-Pyridyl                                                      387  CN         4-Pyridyl                                                      388  CN         2,6-Pyrimidinyl                                                389  CN         1,5-Pyrimidinyl                                                390  CN         2-Thienyl                                                      391  CN         3-Thienyl                                                      392  CN         2-Furyl                                                        393  CN         3-Furyl                                                        394  CN         1-Pyrrolyl                                                     395  CN         1-imidazolyl                                                   396  CN         1,2,4-Triazolyl                                                397  CN         1,3,4-Triazolyl                                                398  CN         4-Thiazolyl                                                    399  CN         2-Benzothiazolyl                                               400  CN         2-Pyridyloxy                                                   401  CN         2-Pyrimidinyloxy                                               402  CN         2-Pyridylthio                                                  403  CN         2-Pyrimidinylthio                                              404  CN         2-Benzothiazolylthio                                           405  CN         Phenylthiomethyl                                               406  CN         2-Pyridylmethyl                                                407  CN         3-Pyridylmethyl                                                408  CN         Furfurytoxy                                                    409  CN         Thienylmethoxy                                                 410  CN         3-Isoxazolylmethoxy                                            411  CN         2-Oxazolylmethoxy                                              412  CN         2-Pyridylmethoxy                                               413  CN         2'-Furyl-2-ethenyl                                             414  CN         2'-Thienyl-2-ethenyl                                           415  CN         3'-Pyridyl-2-ethenyl                                           416  CN         Oxiranyl                                                       417  CN         1-Aziridinyl                                                   418  CN         1-Azetidinyl                                                   419  CN         1-Pyrrolidinyl                                                 420  CN         2-Tetrahydrofuryl                                              421  CN         2-Tetrahydropyranyl                                            422  CN         3-Tetrahydropyranyl                                            423  CN         1-Piperidinyl                                                  424  CN         1-Morpholinyl                                                  425  CN         1-Piperazinyl                                                  426  CN         1,3-Dioxan-2-yl                                                427  CN         3-Tetrahydrothiopyranyl                                        428  CN         2-Dihydropyranyloxy                                            429  CN         2-Tetrahydropyranyloxy                                                                         oil; IR (film):                                                                1439, 1228, 1209,                                                              1050, 1025 767                                 430  CN         (CH.sub.2).sub.4                                               431  CN         (CH.sub.2).sub.5                                               432  CN         (CH.sub.2).sub.6                                               433  CN                                                                        434  CN                                                                        435  CN                                                                                         ##STR21##                                                     436  CN                                                                                         ##STR22##                                                     437  CN                                                                                         ##STR23##                                                     438  CN                                                                                         ##STR24##                                                     439  CN                                                                                         ##STR25##                                                     440  CN                                                                                         ##STR26##                                                     441  CN         CF.sub.3                                                       442  CN         2-Fluoroethyl                                                  443  CN         2,2,2-Trifluoroethyl                                           444  CN         Pentafluoroethyl                                               445  CN         Chloromethyl                                                   446  CN         Dichloromethyl                                                 447  CN         Trichloromethyl                                                448  CN         2-Chloroethyl                                                  449  CN         2,2,2-Trichloroethyl                                           450  CN         Pentachloroethyl                                               451  CN         Cyclopropyl                                                    452  CN         Cyclobutyl                                                     453  CN         Cyclopentyl                                                    454  CN         Cyclohexyl                                                     455  CN         1-Methylcyclopropyl                                            456  CN         2,2-Dimethylcyclo-                                                             propyl                                                         457  CN         1-Methylcyclohexyl                                             458  CN         2,2-Difluorocyclopropyl                                        459  CN         2,2-Dichlorocyclopropyl                                        460  CN         2,2-Dibromocyclopropyl                                         461  CN         2,2-Dichloro-3-                                                                Methylcyclopropyl                                              462  CN         2,2,3,3-Tetrafluoro-                                                           cyclobutyl                                                     463  CN         Ethenyl                                                        464  CN         1-Propenyl                                                     465  CN         2-Methyl-1-propenyl                                            466  CN         4-Methylpent-3-en-1-yl                                         467  CN         2-Propenyl                                                     468  CN         2-Butenyl                                                      469  CN         1-Methyl-2-propenyl                                            470  CN         3-Methyl-2-butenyl                                             471  CN         2,2-Difluoroethenyl                                            472  CN         2,2-Dichloroethenyl                                            473  CN         3,3,3-Trifluoro-                                                               propenyl                                                       474  CN         3,3,3-Trichloro-                                                               propenyl                                                       475  CN         3-Chloro-2-propenyl                                            476  CN         Cyclopent-1-enyl                                               477  CN         Cyclopentadienyl                                               478  CN         Cyclohex-1-enyl                                                479  CN         Pentafluorocyclo-                                                              pentadienyl                                                    480  CN         Pentachlorocyclo-                                                              pentadienyl                                                    481  CN         Styryl                                                         482  CH.sub.3   Methoxymethyl                                                  483  CH.sub.3   Ethoxymethyl                                                   484  CH.sub.3   n-Propoxymethyl                                                485  CH.sub.3   iso-Propoxymethyl                                              486  CH.sub.3   tert.-Butoxymethyl                                             487  CH.sub.3   2-Methoxyprop-2-yl                                             488  CH.sub.3   2-Ethoxyprop-2-yl                                              489  CH.sub.3   2-n-Propoxyprop-2-yl                                           490  CH.sub.3   2-iso-Propoxyprop-2-yl                                         491  CH.sub.3   2-tert.-Butoxyprop-2-yl                                        492  CH.sub.3   Methylthiomethyl                                               493  CH.sub.3   tert.-Butylthiomethyl                                          494  CH.sub.3   2-Methylthioprop-2-yl                                          495  CH.sub.3   2-iso-Propylthioprop-2-                                                        yl                                                             496  CH.sub.3   2-tert.-Butylthioprop-2-                                                       yl                                                             497  CH.sub.3   Methyl          m.p. 68-71° C.;                                                         IR (KBr): 1137,                                                                1298, 1067, 1023,                                                              1007, 771                                      498  CH.sub.3   Ethyl                                                          499  CH.sub.3   n-Propyl                                                       500  CH.sub.3   iso-Propyl                                                     501  CH.sub.3   n-Butyl                                                        502  CH.sub.3   iso-Butyl                                                      503  CH.sub.3   sec.-Butyl                                                     504  CH.sub.3   tert.-Butyl                                                    505  CH.sub.3   n-Hexyl                                                        506  CH.sub.3   n-Decyl                                                        507  CH.sub.3   Cyclopropyl                                                    508  CH.sub.3   Cyclohexyl                                                     509  CH.sub.3   Phenylthiomethyl                                               510  CH.sub.3   2-Phenylthiomethyl                                             511  CH.sub.3   2-(2'-Chlorophenyl-                                                            thio)prop-2-yl                                                 512  CH.sub.3   Ethynyl                                                        513  CH.sub.3   1-Propynyl                                                     514  CH.sub.3   Methoxy                                                        515  CH.sub.3   Ethoxy                                                         516  CH.sub.3   n-Propoxy                                                      517  CH.sub.3   iso-Propoxy                                                    518  CH.sub.3   n-Butoxy                                                       519  CH.sub.3   iso-Butoxy                                                     520  CH.sub.3   sec.-Butoxy                                                    521  CH.sub.3   tert.-Butoxy                                                   522  CH.sub.3   Methylthio                                                     523  CH.sub.3   Ethylthio                                                      524  CH.sub.3   n-Propylthio                                                   525  CH.sub.3   iso-Propylthio                                                 526  CH.sub.3   n-Butylthio                                                    527  CH.sub.3   iso-Butylthio                                                  528  CH.sub.3   sec.-Butylthio                                                 529  CH.sub.3   tert.-Butylthio                                                530  CH.sub.3   Benzylthio                                                     531  CH.sub.3   Trifluoromethoxy                                               532  CH.sub.3   Cyano                                                          533  CH.sub.3   Amino                                                          534  CH.sub.3   Methylamino                                                    535  CH.sub.3   Dimethylamino                                                  536  CH.sub.3   Ethylamino                                                     537  CH.sub.3   Diethylamino                                                   538  CH.sub.3   Di-n-Propylamino                                               539  CH.sub.3   Di-iso-Propylamino                                             540  CH.sub.3   Di-n-Butylamino                                                541  CH.sub.3   Di-iso-Butylamino                                              542  CH.sub.3   Acetyl                                                         543  CH.sub.3   Propion-1-yl                                                   544  CH.sub.3   Butyr-1-yl                                                     545  CH.sub.3   iso-Butyr-1-yl                                                 546  CH.sub.3   Pivaloyl                                                       547  CH.sub.3   Benzoyl                                                        548  CH.sub.3   4-Chlorobenzoyl                                                549  CH.sub.3   Benzylcarbonyl                                                 550  CH.sub.3   Methoxycarbonyl                                                551  CH.sub.3   Ethoxycarbonyl                                                 552  CH.sub.3   n-Propoxycarbonyl                                              553  CH.sub.3   iso-Propoxycarbonyl                                            554  CH.sub.3   n-Butoxycarbonyl                                               555  CH.sub.3   iso-Butoxycarbonyl                                             556  CH.sub.3   sec.-Butoxycarbonyl                                            557  CH.sub.3   tert.-Butoxycarbonyl                                           558  CH.sub.3   n-Hexoxycarbonyl                                               559  CH.sub.3   Phenoxycarbonyl                                                560  CH.sub.3   4-Chlorophenoxy-                                                               carbonyl                                                       561  CH.sub.3   Benzyloxycarbonyl                                              562  CH.sub.3   Aminocarbonyl                                                  563  CH.sub.3   Dimethylamino-                                                                 carbonyl                                                       564  CH.sub.3   Diethylamino-                                                                  carbonyl                                                       565  CH.sub.3   Di-iso-Propylamino-                                                            carbonyl                                                       566  CH.sub.3   Phenylaminocarbonyl                                            567  CH.sub.3   N-Methyl-N-Phenyl-                                                             aminocarbonyl                                                  568  CH.sub.3   Phenyl                                                         569  CH.sub.3   2-Fluorophenyl  m.p.: 89-91° C.;                                                        IR (KBr): 1732,                                                                1071, 1012, 998,                                                               768                                            570  CH.sub.3   3-Fluorophenyl  m.p.: 83-85° C.;                                                        IR (KBr): 1724,                                                                1204, 1067, 1031,                                                              1015, 955                                      571  CH.sub.3   4-Fluorophenyl  m.p.: 76-8° C.;                                                         IR (KBr): 1737,                                                                1510, 1302, 1224,                                                              1072, 1031, 1015,                                                              933                                            572  CH.sub.3   Pentafluorophenyl                                              573  CH.sub.3   2-Chlorophenyl                                                 574  CH.sub.3   3-Chlorophenyl  m.p.: 61-63° C.;                                                        IR (KBr): 1735,                                                                1070, 1015, 1002,                                                              785                                            575  CH.sub.3   4-Chlorophenyl  oil; IR (film):                                                                1708, 1634, 1256,                                                              1129                                           576  CH.sub.3   Pentachlorophenyl                                              577  CH.sub.3   2,3-Dichlorophenyl                                             578  CH.sub.3   2,4-Dichlorophenyl                                             579  CH.sub.3   2,5-Dichlorophenyl                                             580  CH.sub.3   2,6-Dichlorophenyl                                             581  CH.sub.3   3,4-Dichlorophenyl                                             582  CH.sub.3   3,5-Dichlorophenyl                                                                             m.p.: 95-7° C.;                                                         IR (KBr): 1723,                                                                1556, 1224, 1067,                                                              1030, 1014, 957                                583  CH.sub.3   2,3,4-Trichlorophenyl                                                                          m.p.: 118-20° C.                        584  CH.sub.3   2,3,5-Trichlorophenyl                                          585  CH.sub.3   2,3,6-Trichlorophenyl                                          586  CH.sub.3   2,4,5-Trichlorophenyl                                          587  CH.sub.3   2,4,6-Trichlorophenyl                                          588  CH.sub.3   3,4,5-Trichlorophenyl                                          589  CH.sub.3   2,3,4,6-Tetrachloro-                                                           phenyl                                                         590  CH.sub.3   2,3,5,6-Tetrachloro-                                                           phenyl                                                         591  CH.sub.3   2-Bromophenyl                                                  592  CH.sub.3   3-Bromophenyl   m.p.: 80-4° C.;                                                         IR (KBr): 1723,                                                                1556, 1224, 1067,                                                              1030, 1014, 957                                593  CH.sub.3   4-Bromophenyl   m.p.: 73-75° C.;                                                        IR (KBr): 1736,                                                                1071, 1029, 1015,                                                              932                                            594  CH.sub.3   2,4-Dibromophenyl                                              595  CH.sub.3   3-Bromo-4-fluorophenyl                                         596  CH.sub.3   3-Bromo-4-methoxy-                                                             phenyl                                                         597  CH.sub.3   2-Iodophenyl                                                   598  CH.sub.3   3-Iodophenyl                                                   599  CH.sub.3   4-Iodophenyl                                                   600  CH.sub.3   2-Chloro-4-fluorophenyl                                        601  CH.sub.3   2-Chloro-5-fluorophenyl                                        602  CH.sub.3   2-Chloro-6-fluorophenyl                                        603  CH.sub.3   2-Chloro-4-bromophenyl                                         604  CH.sub.3   2-Bromo-4-chlorophenyl                                         605  CH.sub.3   2-Bromo-4-fluorophenyl                                         606  CH.sub.3   3-Bromo-4-chlorophenyl                                         607  CH.sub.3   3-Chloro-4-fluorophenyl                                        608  CH.sub.3   3-Fluoro-4-chlorophenyl                                        609  CH.sub.3   2-Cyanophenyl                                                  610  CH.sub.3   3-Cyanophenyl                                                  611  CH.sub.3   4-Cyanophenyl                                                  612  CH.sub.3   2-Nitrophenyl                                                  613  CH.sub.3   3-Nitrophenyl                                                  614  CH.sub.3   4-Nitrophenyl   m.p.: 88-90° C.;                                                        IR (KBr): 1725,                                                                1512, 1342, 1219,                                                              1068, 1009, 854                                615  CH.sub.3   2-Methylphenyl                                                 616  CH.sub.3   3-Methylphenyl  m.p.: 93-96° C.                         617  CH.sub.3   4-Methylphenyl  m.p.: 82-84° C.;                                                        IR (KBr): 1722,                                                                1068, 1038, 1015,                                                              920                                            618  CH.sub.3   2,4-Dimethylphenyl                                             619  CH.sub.3   2,6-Dimethylphenyl                                             620  CH.sub.3   3,4-Dimethylphenyl                                             621  CH.sub.3   3,5-Dimethylphenyl                                             622  CH.sub.3   2,3,4-Trimethylphenyl                                          623  CH.sub.3   2,3,5-Trimethylphenyl                                          624  CH.sub.3   2,3,6-Trimethylphenyl                                          625  CH.sub.3   2,4,5-Trimethylphenyl                                          626  CH.sub.3   2,4,6-Trimethylphenyl                                          627  CH.sub.3   3,4,5-Trimethylphenyl                                          628  CH.sub.3   Pentamethylphenyl                                              629  CH.sub.3   2-Ethylphenyl                                                  630  CH.sub.3   3-Ethylphenyl                                                  631  CH.sub.3   4-Ethylphenyl                                                  632  CH.sub.3   3,5-Diethylphenyl                                              633  CH.sub.3   2-n-Propylphenyl                                               634  CH.sub.3   3-n-Propylphenyl                                               635  CH.sub.3   4-n-Propylphenyl                                               636  CH.sub.3   2-iso-Propylphenyl                                             637  CH.sub.3   3-iso-Propylphenyl                                             638  CH.sub.3   4-iso-Propylphenyl                                             639  CH.sub.3   2,4-Di-iso-Propyl-                                                             phenyl                                                         640  CH.sub.3   3,5-Di-iso-Propyl-                                                             phenyl                                                         641  CH.sub.3   4-n-Butylphenyl                                                642  CH.sub.3   4-sec.-Butylphenyl                                             643  CH.sub.3   4-iso-Butylphenyl                                              644  CH.sub.3   4-tert.-Butylphenyl                                                                            m.p.: 45-50° C.                         645  CH.sub.3   3-tert.-Butylphenyl                                            646  CH.sub.3   2-tert.-Butylphenyl                                            647  CH.sub.3   2,4-Di-tert.-Butyl-                                                            phenyl                                                         648  CH.sub.3   3,5-Di-tert.-Butyl-                                                            phenyl                                                         649  CH.sub.3   4-n-Hexylphenyl                                                650  CH.sub.3   4-n-Dodecylphenyl                                              651  CH.sub.3   2-Methyl-4-tert.-Butyl-                                                        phenyl                                                         652  CH.sub.3   2-Methyl-6-tert.-Butyl-                                                        phenyl                                                         653  CH.sub.3   2-Methyl-4-iso-Propyl-                                                         phenyl                                                         654  CH.sub.3   2-Methyl-4-Cyclohexyl-                                                         phenyl                                                         655  CH.sub.3   2-Methyl-4-Phenyl-                                                             phenyl                                                         656  CH.sub.3   2-Methyl-4-Benzyl-                                                             phenyl                                                         657  CH.sub.3   2-Methyl-4-Phenoxy-                                                            phenyl                                                         658  CH.sub.3   2-Methyl-4-Benzyloxy-                                                          phenyl                                                         659  CH.sub.3   2-Methyl-3-Chloro-                                                             phenyl                                                         660  CH.sub.3   2-Methyl-4-Chloro-                                                             phenyl                                                         661  CH.sub.3   2-Methyl-5-Chloro-                                                             phenyl                                                         662  CH.sub.3   2-Methyl-6-chloro-                                                             phenyl                                                         663  CH.sub.3   2-Methyl-4-fluoro-                                                             phenyl                                                         664  CH.sub.3   2-Methyl-3-bromo-                                                              phenyl                                                         665  CH.sub.3   2-Methyl-4-bromo-                                                              phenyl                                                         666  CH.sub.3   2-Methyl-3-methoxy-                                                            phenyl                                                         667  CH.sub.3   2-Methyl-4-methoxy-                                                            phenyl                                                         668  CH.sub.3   2-Methyl-5-methoxy-                                                            phenyl                                                         669  CH.sub.3   2-Methyl-6-methoxy-                                                            phenyl                                                         670  CH.sub.3   2-Methyl-4-iso-                                                                Propoxyphenyl                                                  671  CH.sub.3   2-Methyl-2,5-                                                                  dimethoxyphenyl                                                672  CH.sub.3   2-Methoxyphenyl m.p.: 74-6° C.;                                                         IR (KBr): 1741,                                                                1433, 1295, 1249,                                                              1224, 1067, 1022,                                                              878                                            673  CH.sub.3   3-Methoxyphenyl                                                674  CH.sub.3   4-Methoxyphenyl m.p.: 89-91° C.                         675  CH.sub.3   2,3-Dimethoxyphenyl                                            676  CH.sub.3   2,4-Dimethoxyphenyl                                            677  CH.sub.3   2,5-Dimethoxyphenyl                                            678  CH.sub.3   2,6-Dimethoxyphenyl                                            679  CH.sub.3   3,4-Dimethoxyphenyl                                            680  CH.sub.3   3,5-Dimethoxyphenyl                                            681  CH.sub.3   3,6-Dimethoxyphenyl                                            682  CH.sub.3   2,3,4-Trimethoxy-                                                              phenyl                                                         683  CH.sub.3   2,3,5-Trimethoxy-                                                              phenyl                                                         684  CH.sub.3   2,3,6-Trimethoxy-                                                              phenyl                                                         685  CH.sub.3   2,4,5-Trimethoxy-                                                              phenyl                                                         686  CH.sub.3   2,4,6-Trimethoxy-                                                              phenyl                                                         687  CH.sub.3   3,4,5-Trimethoxy-                                                              phenyl                                                         688  CH.sub.3   2-Ethoxyphenyl                                                 689  CH.sub.3   3-Ethoxyphenyl                                                 690  CH.sub.3   4-Ethoxyphenyl                                                 691  CH.sub.3   2-iso-Propoxyphenyl                                            692  CH.sub.3   3-iso-Propoxyphenyl                                            693  CH.sub.3   4-iso-Propoxyphenyl                                            694  CH.sub.3   3-tert.-Butoxyphenyl                                           695  CH.sub.3   4-tert.-Butoxyphenyl                                           696  CH.sub.3   2-Trifluoromethoxy-                                                            phenyl                                                         697  CH.sub.3   3-Trifluoromethoxy-                                                            phenyl                                                         698  CH.sub.3   4-Trifluoromethoxy-                                                            phenyl                                                         699  CH.sub.3   3-(1',1',2',2'-Tetra-                                                          fluoro)ethoxyphenyl                                            700  CH.sub.3   4-(1',1',2',2'-Tetra-                                                          fluoro)ethoxyphenyl                                            701  CH.sub.3   2-Chloromethylphenyl                                           702  CH.sub.3   3-Chloromethylphenyl                                           703  CH.sub.3   4-Chloromethylphenyl                                           704  CH.sub.3   2-Trifluoromethyl-                                                                             m.p.: 78-80° C.;                                        phenyl          IR (KBr): 1741,                                                                1315, 1116, 1068,                                                              1010                                           705  CH.sub.3   3-Trifluoromethyl-                                                                             m.p.: 70-72° C.;                                        phenyl          IR (KBr): 1740,                                                                1291, 1281, 1164,                                                              1124, 1073, 1010                               706  CH.sub.3   4-Trifluoromethyl-                                                                             m.p.: 57-58° C.;                                        phenyl          (IR (KBr): 1728,                                                               1333, 1318, 1106,                                                              1069, 986                                      707  CH.sub.3   2-(Methoxyimino-                                                               methyl)phenyl                                                  708  CH.sub.3   3-(Methoxyimino-                                                               methyl)phenyl                                                  709  CH.sub.3   4-(Methoxyimino-                                                               methyl)phenyl                                                  710  CH.sub.3   2-(Ethoxyimino-                                                                methyl)phenyl                                                  711  CH.sub.3   3-(Ethoxyimino-                                                                methyl)phenyl                                                  712  CH.sub.3   4-(Ethoxyimino-                                                                methyl)phenyl                                                  713  CH.sub.3   2-(n-Propoxyimino-                                                             methyl)phenyl                                                  714  CH.sub.3   3-(n-Propoxyimino-                                                             methyl)phenyl                                                  715  CH.sub.3   4-(n-Propoxyimino-                                                             methyl)phenyl                                                  716  CH.sub.3   2-(iso-Propoxyimino-                                                           methyl)phenyl                                                  717  CH.sub.3   3-(iso-Propoxyimino-                                                           methyl)phenyl                                                  718  CH.sub.3   4-(iso-Propoxyimino-                                                           methyl)phenyl                                                  719  CH.sub.3   2-(n-Butoxyimino-                                                              methyl)phenyl                                                  720  CH.sub.3   3-(n-Butoxyimino-                                                              methyl)phenyl                                                  721  CH.sub.3   4-(n-Butoxyimino-                                                              methyl)phenyl                                                  722  CH.sub.3   2-(iso-Butoxyimino-                                                            methyl)phenyl                                                  723  CH.sub.3   3-(iso-Butoxyimino-                                                            methyl)phenyl                                                  724  CH.sub.3   4-(iso-Butoxyimino-                                                            methyl)phenyl                                                  725  CH.sub.3   2-(tert.-Butoxyimino-                                                          methyl)phenyl                                                  726  CH.sub.3   3-(tert.-Butoxyimino-                                                          methyl)phenyl                                                  727  CH.sub.3   4-(tert.-Butoxyimino-                                                          methyl)phenyl                                                  728  CH.sub.3   2-(n-Pentoxyimino-                                                             methyl)phenyl                                                  729  CH.sub.3   3-(n-Pentoxyimino-                                                             methyl)phenyl                                                  730  CH.sub.3   4-(n-Pentoxyimino-                                                             methyl)phenyl                                                  731  CH.sub.3   2-(n-Hexoxyimino-                                                              methyl)phenyl                                                  732  CH.sub.3   3-(n-Hexoxyimino-                                                              methyl)phenyl                                                  733  CH.sub.3   4-(n-Hexoxyimino-                                                              methyl)phenyl                                                  734  CH.sub.3   2-(Allyloxyimino-                                                              methyl)phenyl                                                  735  CH.sub.3   3-(Allyloxyimino-                                                              methyl)phenyl                                                  736  CH.sub.3   4-(Allyloxyimino-                                                              methyl)phenyl                                                  737  CH.sub.3   2-(Benzyloxyimino-                                                             methyl)phenyl                                                  738  CH.sub.3   3-(Benzyloxyimino-                                                             methyl)phenyl                                                  739  CH.sub.3   4-(Benzyloxyimino-                                                             methyl)phenyl                                                  740  CH.sub.3   2-(Methoxyimino-1'-                                                            ethyl)phenyl                                                   741  CH.sub.3   3-(Methoxyimino-1'-                                                            ethyl)phenyl                                                   742  CH.sub.3   4-(Methoxyimino-1'-                                                            ethyl)phenyl                                                   743  CH.sub.3   2-(Ethoxyimino-1'-                                                             ethyl)phenyl                                                   744  CH.sub.3   3-(Ethoxyimino-1'-                                                             ethyl)phenyl                                                   745  CH.sub.3   4-(Ethoxyimino-1'-                                                             ethyl)phenyl                                                   746  CH.sub.3   2-(n-Propoxyimino-1'-                                                          ethyl)phenyl                                                   747  CH.sub.3   3-(n-Propoxyimino-1'-                                                          ethyl)phenyl                                                   748  CH.sub.3   4-(n-Propoxyimino-1'-                                                          ethyl)phenyl                                                   749  CH.sub.3   2-(n-Butoxyamino-1'-                                                           ethyl)phenyl                                                   750  CH.sub.3   3-(n-Butoxyamino-1'-                                                           ethyl)phenyl                                                   751  CH.sub.3   4-(n-Butoxyamino-1'-                                                           ethyl)phenyl                                                   752  CH.sub.3   2-(n-Pentoxyimino-1'-                                                          ethyl)phenyl                                                   753  CH.sub.3   3-(n-Pentoxyimino-1'-                                                          ethyl)phenyl                                                   754  CH.sub.3   4-(n-Pentoxyimino-1'-                                                          ethyl)phenyl                                                   755  CH.sub.3   2-(n-Hexoxyimino-1'-                                                           ethyl)phenyl                                                   756  CH.sub.3   3-(n-Hexoxyimino-1'-                                                           ethyl)phenyl                                                   757  CH.sub.3   4-(n-Hexoxyimino-1'-                                                           ethyl)phenyl                                                   758  CH.sub.3   2-(Allyloxyimino-1'-                                                           ethyl)phenyl                                                   759  CH.sub.3   3-(Allyloxyimino-1'-                                                           ethyl)phenyl                                                   760  CH.sub.3   4-(Allyloxyimino-1'-                                                           ethyl)phenyl                                                   761  CH.sub.3   2-(Benzyloxyimino-1'-                                                          ethyl)phenyl                                                   762  CH.sub.3   3-(Benzyloxyimino-1'-                                                          ethyl)phenyl                                                   763  CH.sub.3   4-(Benzyloxyimino-1'-                                                          ethyl)phenyl                                                   764  CH.sub.3   2-Phenylphenyl                                                 765  CH.sub.3   3-Phenylphenyl                                                 766  CH.sub.3   4-Phenylphenyl                                                 767  CH.sub.3   2-Phenoxyphenyl                                                768  CH.sub.3   3-Phenoxyphenyl                                                769  CH.sub.3   4-Phenoxyphenyl m.p.: 91-3° C.;                                                         IR (KBr): 1732,                                                                1587, 1491, 1241,                                                              1071, 1014, 995,                                                               769                                            770  CH.sub.3   2-Benzyloxyphenyl                                              771  CH.sub.3   3-Benzyloxyphenyl                                              772  CH.sub.3   4-Benzyloxyphenyl                                              773  CH.sub.3   4-(Imidazol-1'-                                                                yl)phenyl                                                      774  CH.sub.3   4-(Piperazin-1'-                                                               yl)phenyl                                                      775  CH.sub.3   4-(Morpholin-1'-                                                               yl)phenyl                                                      776  CH.sub.3   4-(Piperidin-1'-                                                               yl)phenyl                                                      777  CH.sub.3   4-(Pyridyl-2'-                                                                 oxy)phenyl                                                     778  CH.sub.3   2-Cyclopropylphenyl                                            779  CH.sub.3   3-Cyclopropylphenyl                                            780  CH.sub.3   4-Cyclopropylphenyl                                            781  CH.sub.3   3-Cyclohexylphenyl                                             782  CH.sub.3   4-Cyclohexylphenyl                                                                             m.p.: 53-5° C.                          783  CH.sub.3   4-Oxiranylphenyl                                               784  CH.sub.3   4-(1',3'-Dioxan-2'-                                                            phenyl                                                         785  CH.sub.3   4-(Tetrahydropyran-2-                                                          yloxy)phenyl                                                   786  CH.sub.3   1-Naphthyl                                                     787  CH.sub.3   2-Naphthyl                                                     788  CH.sub.3   9-Anthryl                                                      789  CH.sub.3   1-Naphthoxy                                                    790  CH.sub.3   2-Naphthoxy                                                    791  CH.sub.3   9-Anthroxy                                                     792  CH.sub.3   Phenoxy                                                        793  CH.sub.3   2-Chlorophenoxy                                                794  CH.sub.3   3-Chlorophenoxy                                                795  CH.sub.3   4-Chlorophenoxy                                                796  CH.sub.3   4-Methylphenoxy                                                797  CH.sub.3   4-tert.-Butylphenoxy                                           798  CH.sub.3   4-Methoxyphenoxy                                               799  CH.sub.3   4-Ethoxyphenoxy                                                800  CH.sub.3   4-tert.-Butoxyphenoxy                                          801  CH.sub.3   Phenylthio                                                     802  CH.sub.3   2-Chlorophenylthio                                             803  CH.sub.3   4-Chlorophenylthio                                             804  CH.sub.3   Benzyl                                                         805  CH.sub.3   2-Methylbenzyl                                                 806  CH.sub.3   3-Methylbenzyl                                                 807  CH.sub.3   4-Methylbenzyl                                                 808  CH.sub.3   4-tert.-Butylbenzyl                                            809  CH.sub.3   2-Chlorobenzyl                                                 810  CH.sub.3   3-Chlorobenzyl                                                 811  CH.sub.3   4-Chlorobenzyl                                                 812  CH.sub.3   2,4-Dichlorobenzyl                                             813  CH.sub.3   2,6-Dichlorobenzyl                                             814  CH.sub.3   2,4,6-Trichlorobenzyl                                          815  CH.sub.3   2-Trifluoromethyl-                                                             benzyl                                                         816  CH.sub.3   3-Trifluoromethyl-                                                             benzyl                                                         817  CH.sub.3   4-Trifluoromethyl-                                                             benzyl                                                         818  CH.sub.3   2-Methoxybenzyl                                                819  CH.sub.3   4-Methoxybenzyl                                                820  CH.sub.3   4-tert.-Butoxybenzyl                                           821  CH.sub.3   4-Phenoxybenzyl                                                822  CH.sub.3   1-Phenethyl                                                    823  CH.sub.3   2-Phenethyl                                                    824  CH.sub.3   1-Phenylpropyl                                                 825  CH.sub.3   2-Phenylpropyl                                                 826  CH.sub.3   3-Phenylpropyl                                                 827  CH.sub.3   2-Methyl-2-phenyl-                                                             propyl                                                         828  CH.sub.3   2-Methyl-3-phenyl-                                                             propyl                                                         829  CH.sub.3   4-Phenylbutyl                                                  830  CH.sub.3   2-Phenyl-1-ethenyl                                             831  CH.sub.3   1-Phenyl-1-ethenyl                                             832  CH.sub.3   1-Phenyl-1-propenyl                                            833  CH.sub.3   1-Phenyl-1-propen-2-yl                                         834  CH.sub.3   2,2-Diphenylethenyl                                            835  CH.sub.3   Phenoxymethyl                                                  836  CH.sub.3   2-Pyridyl                                                      837  CH.sub.3   3-Pyridyl                                                      838  CH.sub.3   4-Pyridyl                                                      839  CH.sub.3   2,6-Pyrimidinyl                                                840  CH.sub.3   1,5-Pyrimidinyl                                                841  CH.sub.3   2-Thienyl                                                      842  CH.sub.3   3-Thienyl                                                      843  CH.sub.3   2-Furyl                                                        844  CH.sub.3   3-Furyl                                                        845  CH.sub.3   1-Pyrrolyl                                                     846  CH.sub.3   1-Imidazolyl                                                   847  CH.sub.3   1,2,4-Triazolyl                                                848  CH.sub.3   1,3,4-Triazolyl                                                849  CH.sub.3   4-Thiazolyl                                                    850  CH.sub.3   2-Benzothiazolyl                                               851  CH.sub.3   2-Pyridyloxy                                                   852  CH.sub.3   2-Pyrimidinyloxy                                               853  CH.sub.3   2-Pyridylthio                                                  854  CH.sub.3   2-Pyrimidinylthio                                              855  CH.sub.3   2-Benzothiazolylthio                                           856  CH.sub.3   Phenylthiomethyl                                               857  CH.sub.3   2-Pyridylmethyl                                                858  CH.sub.3   3-Pyridylmethyl                                                859  CH.sub.3   Furfuryloxy                                                    860  CH.sub.3   Thienylmethoxy                                                 861  CH.sub.3   3-Isoxazolylmethoxy                                            862  CH.sub.3   2-Oxazolylmethoxy                                              863  CH.sub.3   2-Pyridylmethoxy                                               864  CH.sub.3   2'-Furyl-2-ethenyl                                             865  CH.sub.3   2'-Thienyl-2-ethenyl                                           866  CH.sub.3   3'-Pyridyl-2-ethenyl                                           867  CH.sub.3   Oxiranyl                                                       868  CH.sub.3   1-Aziridinyl                                                   869  CH.sub.3   1-Azetidinyl                                                   870  CH.sub.3   1-Pyrrolidinyl                                                 871  CH.sub.3   2-Tetrahydrofuryl                                              872  CH.sub.3   2-Tetrahydropyranyl                                            873  CH.sub.3   3-Tetrahydropyranyl                                            874  CH.sub.3   1-Piperidinyl                                                  875  CH.sub.3   1-Morpholinyl                                                  876  CH.sub.3   1-Piperazinyl                                                  877  CH.sub.3   1,3-Dioxan-2-yl                                                878  CH.sub.3   3-Tetrahydrothio-                                                              pyranyl                                                        879  CH.sub.3   2-Dihydropyranyloxy                                            880  CH.sub.3   2-Tetrahydro-                                                                  pyranyloxy                                                     881  CH.sub.3   CF.sub.3                                                       882  CH.sub.3   2-Fluoroethyl                                                  883  CH.sub.3   2,2,2-Trifluoroethyl                                           884  CH.sub.3   Pentafluoroethyl                                               885  CH.sub.3   Chloromethyl                                                   886  CH.sub.3   Dichloromethyl                                                 887  CH.sub.3   Trichloromethyl                                                888  CH.sub.3   2-Chloroethyl                                                  889  CH.sub.3   2,2,2-Trichloroethyl                                           890  CH.sub.3   Pentachloroethyl                                               891  CH.sub.3   Cyclopropyl                                                    892  CH.sub.3   Cyclobutyl                                                     893  CH.sub.3   Cyclopentyl                                                    894  CH.sub.3   Cyclohexyl                                                     895  CH.sub.3   1-Methylcyclopropyl                                            896  CH.sub.3   2,2-Dimethylcyclopropyl                                        897  CH.sub.3   1-Methylcyclohexyl                                             898  CH.sub.3   2,2-Difluorocyclopropyl-                                       899  CH.sub.3   2,2-Dichlorocyclopropyl                                        900  CH.sub.3   2,2-Dibromocyclopropyl                                         901  CH.sub.3   2,2-Dichloro-3-                                                                Methylcyclopropyl                                              902  CH.sub.3   2,2,3,3-Tetrafluoro-                                                           cyclobutyl                                                     903  CH.sub.3   Ethenyl                                                        904  CH.sub.3   1-Propenyl                                                     905  CH.sub.3   2-Methyl-1-propenyl                                            906  CH.sub.3   4-Methylpent-3-en-1-yl                                         907  CH.sub.3   2-Propenyl                                                     908  CH.sub.3   2-Butenyl                                                      909  CH.sub.3   1-Methyl-2-propenyl                                            910  CH.sub.3   3-Methyl-2-butenyl                                             911  CH.sub.3   2,2-Difluoroethenyl                                            912  CH.sub.3   2,2-Dichloroethenyl                                            913  CH.sub.3   3,3,3-Trifluoropropenyl                                        914  CH.sub.3   3,3,3-Trichloropropenyl                                        915  CH.sub.3   3-Chloro-2-propenyl                                            916  CH.sub.3   Cyclopent-1-enyl                                               917  CH.sub.3   Cyclopentadienyl                                               918  CH.sub.3   Cyclohex-1-enyl                                                919  CH.sub.3   Pentafluorocyclo-                                                              pentadienyl                                                    920  CH.sub.3   Pentachlorocyclo-                                                              pentadienyl                                                    921  Phenyl     Phenyl                                                         922  Phenyl     2-Fluorophenyl                                                 923  Phenyl     4-Fluorophenyl                                                 924  Phenyl     2-Chlorophenyl                                                 925  Phenyl     3-Chlorophenyl                                                 926  Phenyl     4-Chlorophenyl                                                 927  Phenyl     3,4-Dichlorophenyl                                             928  Phenyl     4-Nitrophenyl                                                  929  Phenyl     2-CF.sub.3 -Phenyl                                             930  Phenyl     3-CF.sub.3 -Phenyl                                             931  Phenyl     4-CF.sub.3 -Phenyl                                             932  Phenyl     2-Methylphenyl                                                 933  Phenyl     3-Methylphenyl                                                 934  Phenyl     4-Methylphenyl                                                 935  Phenyl     2,4-Dimethylphenyl                                             936  Phenyl     4-tert.-Butylphenyl                                            937  Phenyl     4-Methoxyphenyl                                                938  4-Fluoro-  4-Fluorophenyl                                                      phenyl                                                                    939  2-Fluoro-  4-Fluorophenyl                                                      phenyl                                                                    940  2-Chloro-  4-Fluorophenyl                                                      phenyl                                                                    941  2-Chloro-  2-Chlorophenyl                                                      phenyl                                                                    942  3-Chloro-  3-Chlorophenyl                                                      phenyl                                                                    943  4-Chloro-  4-Chlorophenyl                                                      phenyl                                                                    944  2-Chloro-  4-Chlorophenyl                                                      phenyl                                                                    945  4-Methoxy- 4-Methoxyphenyl                                                     phenyl                                                                    946  4-Dimethyl-                                                                               4-Dimethylamino-                                                    aminophenyl                                                                               phenyl                                                         947  Phenyl     Naphthyl                                                       948  Ethyl      Ethyl                                                          949  Ethyl      n-Propyl                                                       950  Ethyl      iso-Propyl                                                     951  Ethyl      n-Butyl                                                        952  Ethyl      iso-Butyl                                                      953  Ethyl      2-Methyl-butyl                                                 954  Ethyl      Benzyl                                                         955  n-Propyl   n-Propyl                                                       956  iso-Propyl iso-Propyl                                                     957  n-Butyl    n-Butyl                                                        958  iso-Butyl  iso-Butyl                                                      959  tert.-Butyl                                                                               tert.-Butyl                                                    960  Benzyl     Benzyl                                                         961  Penta-     Pentachloroethyl                                                    chloroethyl                                                               962  n-Hexyl    n-Hexyl                                                        963  Ethoxy-    Ethoxycarbonyl                                                      carbonyl                                                                  964  Phenyl     Benzoyl                                                        965  Ethyl      Phenyl                                                         966  n-Butyl    Phenyl                                                         967  Styryl     Styryl                                                         968  2-Pyridyl  2-Pyridyl                                                      969  3-Pyridyl  3-Pyridyl                                                      970  Ethyl      2-Pyridyl       m.p.: 84-86° C.                         971                                                                                  ##STR27##                 m.p.: 103-105° C.                       ______________________________________                                    

    TABLE III       -       ##STR28##                                                                               N      o. X Y R.sup.1 R.sup.2 =       H R.sup.3 R.sup.4 Data       1 CHSCH.sub.3 O CH.sub.3  CF.sub.3 Phenyl       2 CHSCH.sub.3 O CH.sub.3  Cyclopropyl Phenyl       3 CHSCH.sub.3 O CH.sub.3  Cyclopropyl 4-Chlorophenyl       4 CHSCH.sub.3 O CH.sub.3  Cyclopropyl 4-Methoxyphenyl       5 CHSCH.sub.3 O CH.sub.3  Cyclopropyl 4-tert.-Butylphenyl       6 CHSCH.sub.3 O CH.sub.3  CN Methylthio       7 CHSCH.sub.3 O CH.sub.3  CN 2-Methoxyprop-2-yl       8 CHSCH.sub.3 O CH.sub.3  CN 2-Methylthloprop-2-yl       9 CHSCH.sub.3 O CH.sub.3  CN Phenylthio       10 CHSCH.sub.3 O CH.sub.3  CN iso-Propyl       11 CHSCH.sub.3 O CH.sub.3  CN CN       12 CHSCH.sub.3 O CH.sub.3  CN Acetyl       13 CHSCH.sub.3 O CH.sub.3  CN Benzoyl       14 CHSCH.sub.3 O CH.sub.3  CN Methoxycarbonyl       15 CHSCH.sub.3 O CH.sub.3  CN Phenyl       16 CHSCH.sub.3 O CH.sub.3  CN 2-Chlorophenyl       17 CNSCH.sub.3 O CH.sub.3  CN 4-Chlorophenyl       18 CHSCH.sub.3 O CH.sub.3  CN 2-Methylphenyl       19 CHSCH.sub.3 O CH.sub.3  CN 4-tert.-Butylphenyl       20 CHSCH.sub.3 O CH.sub.3  CN 4-(n-Butoxylminomethyl)phenyl       21 CHSCH.sub.3 O CH.sub.3  CN 2-Pyridyl       22 CNSCH.sub.3 O CH.sub.3  CN Styryl       23 CHSCH.sub.3 O CH.sub.3  CN 1-Propenyl       24 CHSCH.sub.3 O CH.sub.3  CH.sub.3 Phenylthio       25 CHSCH.sub.3 O CH.sub.3  CH.sub.3 Benzyl       26 CHSCH.sub.3 O CH.sub.3  CH.sub.3 tert.-Butyl       27 CHSCH.sub.3 O CH.sub.3  CH.sub.3 iso-Propyl       28 CHSCH.sub.3 O CH.sub.3  CH.sub.3 2-Methylbutyl       29 CHSCH.sub.3 O CH.sub.3  CH.sub.3 iso-Butyl       30 CHSCH.sub.3 O CH.sub.3  CH.sub.3 Phenyl       31 CHSCH.sub.3 O CH.sub.3  CH.sub.3 2-Chlorophenyl       32 CHSCH.sub.3 O CH.sub.3  CH.sub.3 4-Chlorophenyl       33 CHSCH.sub.3 O CH.sub.3  CH.sub.3 2-Methylphenyl       34 CHSCH.sub.3 O CH.sub.3  CH.sub.3 Naphthyl       35 CHSCH.sub.3 O CH.sub.3  CH.sub.3 1-Pyridyl       36 CHSCH.sub.3 O CH.sub.3  iso-Butyl iso-Butyl       37 CHSCH.sub.3 O CH.sub.3  Phenyl Phenyl       38 CHSCH.sub.3 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2       CH.sub.2            39 CHSCH.sub.3 O CH.sub.3 CH.sub.2 CH.sub.2      CH.sub.2 CH.sub.2       CH.sub.2                                                40 CHCH.sub.3 O C      H.sub.3 CF.sub.3 Phenyl       41 CHCH.sub.3 O CH.sub.3 Cyclopropyl Phenyl       42 CHCH.sub.3 O CH.sub.3 Cyclopropyl 4-Chlorophenyl       43 CHCH.sub.3 O CH.sub.3 Cyclopropyl 4-Methoxyphenyl       44 CHCH.sub.3 O CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl       45 CHCH.sub.3 O CH.sub.3 CN Methylthio       46 CHCH.sub.3 O CH.sub.3 CN 2-Methoxyprop-2-yl IR (film): 1717,13      36,1367,1256,1210,1179,             1070,1037,1009,759       47 CHCH.sub.3 O CH.sub.3 CN 2-Methylthloprop-2-yl .sup.1       H-NMR (CDCl.sub.3): δ =       1.45s, 1.6d, 1.8s, 3.7s,                         5.1s, 7.1-7.5m               48 CHCH.sub.3 O CH.sub.3 CN Phenylthio       49 CHCH.sub.3 O CH.sub.3 CN iso-Propyl .sup.1 H-NMR (CDCl.sub.3):      δ =       1.2d, 1.6d, 2.7m, 3.67s,      5.1s, 7.0-7.5m       50 CHCH.sub.3 O CH.sub.3 CN CN       51 CHCH.sub.3 O CH.sub.3 CN Acetyl       52 CHCH.sub.3 O CH.sub.3 CN Benzoyl       53 CHCH.sub.3 O CH.sub.3 CN Methoxycarbonyl       54 CHCH.sub.3 O CH.sub.3 CN Phenyl .sup.1 H-NMR (CDCl.sub.3): δ =      1.6d, 3.7s, 5.2s, 7.0-1.8m       55 CHCH.sub.3 O CH.sub.3 CN 2-Chlorophenyl       56 CHCH.sub.3 O CH.sub.3 CN 4-Chlorophenyl       57 CHCH.sub.3 O CH.sub.3 CN 2-Methylphenyl       58 CHCH.sub.3 O CH.sub.3 CN 4-tert.-Butylphenyl       59 CHCH.sub.3 O CH.sub.3 CN 4-(n-Butoxylmlnomethyl)phenyl       60 CHCH.sub.3 O CH.sub.3 CN 2-Pyridyl       61 CHCH.sub.3 O CH.sub.3 CN Styryl       62 CHCH.sub.3 O CH.sub.3 CN 1-Propenyl       63 CHCH.sub.3 O CH.sub.3 CH.sub.3 Phenylthio       64 CHCH.sub.3 O CH.sub.3 CH.sub.3 Benzyl       65 CHCH.sub.3 O CH.sub.3 CH.sub.3 tert.-Butyl       66 CHCH.sub.3 O CH.sub.3 CH.sub.3 iso-Propyl       67 CHCH.sub.3 O CH.sub.3 CH.sub.3 2-Methylbutyl       68 CHCH.sub.3 O CH.sub.3 CH.sub.3 iso-Butyl       69 CHCH.sub.3 O CH.sub.3 CH.sub.3 Phenyl       70 CHCH.sub.3 O CH.sub.3 CH.sub.3 2-Chlorophenyl       71 CHCH.sub.3 O CH.sub.3 CH.sub.3 4-Chlorophenyl IR (film): 1716,13      90,13 34,1253,1206,1096,             1036,1012,820,760       72 CHCH.sub.3 O CH.sub.3 CH.sub.3 2-Methylphenyl       73 CHCH.sub.3 O CH.sub.3 CH.sub.3 Naphthyl       74 CHCH.sub.3 O CH.sub.3 CH.sub.3 1-Pyridyl       75 CHCH.sub.3 O CH.sub.3 iso-Butyl iso-Butyl       76 CHCH.sub.3 O CH.sub.3 Phenyl Phenyl       77 CHCH.sub.3 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2       CH.sub.2             78 CHCH.sub.3 O CH.sub.3 CH.sub.2 CH.sub.2      CH.sub.2 CH.sub.2       CH.sub.2                                                79 CH.sub.2 O      CH.sub.3 CF.sub.3 Phenyl       80 CH.sub.2 O CH.sub.3 Cyclopropyl Phenyl       81 CH.sub.2 O CH.sub.3 Cyclopropyl 4-Chlorophenyl       82 CH.sub.2 O CH.sub.3 Cyclopropyl 4-Methoxyphenyl       83 CH.sub.2 O CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl       84 CH.sub.2 O CH.sub.3 CN Methylthio       85 CH.sub.2 O CH.sub.3 CN 2-Methoxyprop-2-yl       86 CH.sub.2 O CH.sub.3 CN 2-Methylthloprop-2-yl       87 CH.sub.2 O CH.sub.3 CN Phenylthio       88 CH.sub.2 O CH.sub.3 CN iso-Propyl       89 CH.sub.2 O CH.sub.3 CN CN       90 CH.sub.2 O CH.sub.3 CN Acetyl       91 CH.sub.2 O CH.sub.3 CN Benzoyl       92 CH.sub.2 O CH.sub.3 CN Methoxycarbonyl       93 CH.sub.2 O CH.sub.3 CN Phenyl       94 CH.sub.2 O CH.sub.3 CN 2-Chlorophenyl       95 CH.sub.2 O CH.sub.3 CN 4-Chlorophenyl       96 CH.sub.2 O CH.sub.3 CN 2-Methylphenyl       97 CH.sub.2 O CH.sub.3 CN 4-tert.-Butylphenyl       98 CH.sub.2 O CH.sub.3 CN 4-(n-Butoxylminomethyl)phenyl       99 CH.sub.2 O CH.sub.3 CN 2-Pyridyl       100 CH.sub.2 O CH.sub.3 CN Styryl       101 CH.sub.2 O CH.sub.3 CN 1-Propenyl       102 CH.sub.2 O CH.sub.3 CH.sub.3 Phenylthio       103 CH.sub.2 O CH.sub.3 CH.sub.3 Benzyl       104 CH.sub.2 O CH.sub.3 CH.sub.3 tert.-Butyl       105 CH.sub.2 O CH.sub.3 CH.sub.3 iso-Propyl       106 CH.sub.2 O CH.sub.3 CH.sub.3 2-Methylbutyl       107 CH.sub.2 O CH.sub.3 CH.sub.3 iso-Butyl       108 CH.sub.2 O CH.sub.3 CH.sub.3 Phenyl       109 CH.sub.2 O CH.sub.3 CH.sub.3 2-Chlorophenyl       110 CH.sub.2 O CH.sub.3 CH.sub.3 4-Chlorophenyl       111 CH.sub.2 O CH.sub.3 CH.sub.3 2-methylphenyl       112 CH.sub.2 O CH.sub.3 CH.sub.3 Naphthyl       113 CH.sub.2 O CH.sub.3 CH.sub.3 1-Pyridyl       114 CH.sub.2 O CH.sub.3 iso-Butyl iso-Butyl       115 CH.sub.2 O CH.sub.3 Phenyl Phenyl       116 CH.sub.2 O CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2       CH.sub.2              117 CH.sub.2 O CH.sub.3 CH.sub.2 CH.sub.2      CH.sub.2 CH.sub.2       CH.sub.2                                                118 NOCH.sub.3      S CH.sub.3 CF.sub.3 Phenyl       119 NOCH.sub.3 S CH.sub.3 Cyclopropyl Phenyl       120 NOCH.sub.3 S CH.sub.3 Cyclopropyl 4-Chlorophenyl       121 NOCH.sub.3 S CH.sub.3 Cyclopropyl 4-Methoxyphenyl       122 NOCH.sub.3 S CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl       123 NOCH.sub.3 S CH.sub.3 CN Methylthio       124 NOCH.sub.3 S CH.sub.3 CN 2-Methoxyprop-2-yl       125 NOCH.sub.3 S CH.sub.3 CN 2-Methylthioprop-2-yl       126 NOCH.sub.3 S CH.sub.3 CN Phenylthio       127 NOCH.sub.3 S CH.sub.3 CN iso-Propyl       128 NOCH.sub.3 S CH.sub.3 CN CN       129 NOCH.sub.3 S CH.sub.3 CN Acetyl       130 NOCH.sub.3 S CH.sub.3 CN Benzoyl       131 NOCH.sub.3 S CH.sub.3 CN Methoxycarbonyl       132 NOCH.sub.3 S CH.sub.3 CN Phenyl       133 NOCH.sub.3 S CH.sub.3 CN 2-Chlorophenyl       134 NOCH.sub.3 S CH.sub.3 CN 4-Chlorophenyl       135 NOCH.sub.3 S CH.sub.3 CN 2-Methylphenyl       136 NOCH.sub.3 S CH.sub.3 CN 4-tert.-Butylphenyl       137 NOCH.sub.3 S CH.sub.3 CN 4-(n-Butoxylminomethyl)phenyl       138 NOCH.sub.3 S CH.sub.3 CN 2-Pyridyl       139 NOCH.sub.3 S CH.sub.3 CN Styryl       140 NOCH.sub.3 S CH.sub.3 CN 1-Propenyl       141 NOCH.sub.3 S CH.sub.3 CH.sub.3 Phenylthio       142 NOCH.sub.3 S CH.sub.3 CH.sub.3 Benzyl       143 NOCH.sub.3 S CH.sub.3 CH.sub.3 tert.-Butyl       144 NOCH.sub.3 S CH.sub.3 CH.sub.3 iso-Propyl       145 NOCH.sub.3 S CH.sub.3 CH.sub.3 2-Methylbutyl       146 NOCH.sub.3 S CH.sub.3 CH.sub.3 iso-Butyl       147 NOCH.sub.3 S CH.sub.3 CH.sub.3 Phenyl       148 NOCH.sub.3 S CH.sub.3 CH.sub.3 2-Chlorophenyl       149 NOCH.sub.3 S CH.sub.3 CH.sub.3 4-Chlorophenyl       150 NOCH.sub.3 S CH.sub.3 CH.sub.3 2-Methylphenyl       151 NOCH.sub.3 S CH.sub.3 CH.sub.3 Naphthyl       152 NOCH.sub.3 S CH.sub.3 CH.sub.3 1-Pyridyl       153 NOCH.sub.3 S CH.sub.3 iso-Butyl iso-Butyl       154 NOCH.sub.3 S CH.sub.3 Phenyl Phenyl       155 NOCH.sub.3 S CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2       CH.sub.2            156 NOCH.sub.3 S CH.sub.3 CH.sub.2 CH.sub.2      CH.sub.2 CH.sub.2       CH.sub.2                                                157 NOCH.sub.3      NH CH.sub.3 CF.sub.3 Phenyl       158 NOCH.sub.3 NH CH.sub.3 Cyclopropyl Phenyl       159 NOCH.sub.3 NH CH.sub.3 Cyclopropyl 4-Chlorophenyl m.p.: 71-74.degree      .       C.            IR (KBr): 3348,1663,1529,1042,1030,982       160 NOCH.sub.3 NH CH.sub.3 Cyclopropyl 4-Methoxyphenyl       161 NOCH.sub.3 NH CH.sub.3 Cyclopropyl 4-tert.-Butylphenyl       162 NOCH.sub.3 NH CH.sub.3 CN Methylthio       163 NOCH.sub.3 NH CH.sub.3 CN 2-Methoxyprop-2-yl       164 NOCH.sub.3 NH CH.sub.3 CN 2-Methylthioprop-2-yl       165 NOCH.sub.3 NH CH.sub.3 CN Phenylthio       166 NOCH.sub.3 NH CH.sub.3 CN iso-Propyl       167 NOCH.sub.3 NH CH.sub.3 CN CN       168 NOCH.sub.3 NH CH.sub.3 CN Acetyl       169 NOCH.sub.3 NH CH.sub.3 CN Benzoyl       170 NOCH.sub.3 NH CH.sub.3 CN Methoxycarbonyl       171 NOCH.sub.3 NH CH.sub.3 CN Phenyl       172 NOCH.sub.3 NH CH.sub.3 CN 2-Chlorophenyl       173 NOCH.sub.3 NH CH.sub.3 CN 4-Chlorophenyl       174 NOCH.sub.3 NH CH.sub.3 CN 2-Methylphenyl       175 NOCH.sub.3 NH CH.sub.3 CN 4-tert.-Butylphenyl       176 NOCH.sub.3 NH CH.sub.3 CN 4-(n-Butoxyiminomethyl)phenyl       177 NOCH.sub.3 NH CH.sub.3 CN 2-Pyridyl       178 NOCH.sub.3 NH CH.sub.3 CN Styryl       179 NOCH.sub.3 NH CH.sub.3 CN 1-Propenyl       180 NOCH.sub.3 NH CH.sub.3 CH.sub.3 Phenylthio       181 NOCH.sub.3 NH CH.sub.3 CH.sub.3 Benzyl       182 NOCH.sub.3 NH CH.sub.3 CH.sub.3 tert.-Butyl       183 NOCH.sub.3 NH CH.sub.3 CH.sub.3 iso-Propyl       184 NOCH.sub.3 NH CH.sub.3 CH.sub.3 2-Methylbutyl       185 NOCH.sub.3 NH CH.sub.3 CH.sub.3 iso-Butyl       186 NOCH.sub.3 NH CH.sub.3 CH.sub.3 Phenyl       187 NOCH.sub.3 NH CH.sub.3 CH.sub.3 2-Chlorophenyl       188 NOCH.sub.3 NH CH.sub.3 CH.sub.3 4-Chlorophenyl m.p.: 119-121°       C.             IR (KOr): 3421,1676,1037,985,933,752       189 NOCH.sub.3 NH CH.sub.3 CH.sub.3 2-Methylphenyl       No. X Y R.sup.1 R.sup.2 R.sup.3 R.sup.4 Data       190 NOCH.sub.3 NH CH.sub.3 H CH.sub.3 Naphthyl       191 NOCH.sub.3 NH CH.sub.3 H CH.sub.3 1-Pyridyl       192 NOCH.sub.3 NH CH.sub.3 H iso-Butyl iso-Butyl       193 NOCH.sub.3 NH CH.sub.3 H Phenyl Phenyl       194 NOCH.sub.3 NH CH.sub.3 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2             195 NOCH.sub.3 NH CH.sub.3 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2      CH.sub.2       196 NOCH.sub.3 O C.sub.2       H.sub.5 H CH.sub.3 Phenyl                       197 CHOCH.sub.3 O      C.sub.2       H.sub.5 H CH.sub.3 Phenyl                                         198      NOCH.sub.3 O n-C.sub.3       H.sub.5 H CH.sub.3 Phenyl                          199 CHOCH.sub.3 O      n-C.sub.3       H.sub.5 H CH.sub.3 Phenyl                                       200      CHC.sub.2       H.sub.5 O CH.sub.3 H CH.sub.3 Phenyl                            201      NOCH.sub.3 O CH.sub.3 CH.sub.3 CH.sub.3 Phenyl       202 CHOCH.sub.3 O CH.sub.3 CH.sub.3 CH.sub.3 Phenyl       203 NOCH.sub.3 O CH.sub.3 CH.sub.3 CN Phenyl       204 CHOCH.sub.3 O CH.sub.3 CH.sub.3 CN Phenyl       205 CHSCH.sub.3 O CH.sub.3 H H Phenyl       206 CHCH.sub.3 O CH.sub.3 H H Phenyl       207 CH.sub.2 O CH.sub.3 H H Phenyl       208 NOCH.sub.3 S CH.sub.3 H H Phenyl       209 CHOCH.sub.3 S CH.sub.3 H H Phenyl       210 CHOCH.sub.3 NH CH.sub.3 H H Phenyl       211 NOCH.sub.3 NH CH.sub.3 H H Phenyl       212 CHOCH.sub.3 S CH.sub.3 H CN Methylthio       No. X Y R.sup.1 R.sup.2 =       H R.sup.3 R.sup.4 Data       213 CHOCH.sub.3 S CH.sub.3  CN 2-Methoxyprop-2-yl       214 CHOCH.sub.3 S CH.sub.3  CN 2-Methylthloprop-2-yl       215 CHOCH.sub.3 S CH.sub.3  CN Phenylthio       216 CHOCH.sub.3 S CH.sub.3  CN iso-Propyl       217 CHOCH.sub.3 S CH.sub.3  CN CN       218 CHOCH.sub.3 S CH.sub.3  CN Acthyl       219 CHOCH.sub.3 S CH.sub.3  CN Benzoyl       220 CHOCH.sub.3 S CH.sub.3  CN Methoxycarbonyl       221 CHOCH.sub.3 S CH.sub.3  CN Phenyl       222 CHOCH.sub.3 S CH.sub.3  CN 2-Chlorophenyl       223 CHOCH.sub.3 S CH.sub.3  CN 4-Chlorophenyl       224 CHOCH.sub.3 S CH.sub.3  CN 2-methylphenyl       225 CHOCH.sub.3 S CH.sub.3  CN 4-tert.-Butylphenyl       226 CHOCH.sub.3 S CH.sub.3  CN 4-(n-Butoxyiminomethyl)phenyl       227 CHOCH.sub.3 S CH.sub.3  CN 2-Pyridyl       228 CHOCH.sub.3 S CH.sub.3  CN Styryl       229 CHOCH.sub.3 S CH.sub.3  CN 1-Propenyl       230 CHOCH.sub.3 NH CH.sub.3  CN Methylthio       231 CHOCH.sub.3 NH CH.sub.3  CN 2-Methoxyprop-2-yl       232 CHOCH.sub.3 NH CH.sub.3  CN 2-Methylthioprop-2-yl       233 CHOCH.sub.3 NH CH.sub.3  CN Phenylthio       234 CHOCH.sub.3 NH CH.sub.3  CN iso-Propyl       235 CHOCH.sub.3 NH CH.sub.3  CN CN       236 CHOCH.sub.3 NH CH.sub.3  CN Acthyl       237 CHOCH.sub.3 NH CH.sub.3  CN Benzoyl       238 CHOCH.sub.3 NH CH.sub.3  CN Methoxycarbonyl       239 CHOCH.sub.3 NH CH.sub.3  CN Phenyl       240 CHOCH.sub.3 NH CH.sub.3  CN 2-Chlorophenyl       241 CHOCH.sub.3 NH CH.sub.3  CN 4-Chlorophenyl       242 CHOCH.sub.3 NH CH.sub.3  CN 2-Methylphenyl       243 CHOCH.sub.3 NH CH.sub.3  CN 4-tert.-Butylphenyl       244 CHOCH.sub.3 NH CH.sub.3  CN 4-(n-Butoxylminomethyl)phenyl       245 CHOCH.sub.3 NH CH.sub.3  CN 2-Pyridyl       246 CHOCH.sub.3 NH CH.sub.3  CN Styryl       247 CHOCH.sub.3 NH CH.sub.3  CN 1-Propenyl       248 NOCH.sub.3 NH CH.sub.3  CH.sub.3 3-Chlorphenyl m.p.: 71-74°      C.;       249 NOCH.sub.3 NH CH.sub.3  CH.sub.3 3,5-Dichlorphenyl m.p.: 94-97.degre      e.       C.;      250 NOCH.sub.3 NH CH.sub.3  CH.sub.3 2,3,4-Trlchlorphenyl m.p.: 110-112.d      egree.       C.;                                                                251  O      NCH.sub.3 NH CH.sub.3  CH.sub.3 3-Gromphenyl m.p.: 74-77° C.;           252 NOCH.sub.3 NH CH.sub.3  CH.sub.3 4-Methylphenyl m.p.: 69-72.degr      ee.       C.;      253 NOCH.sub.3 NH CH.sub.3  CH.sub.3 4-Nitrophenyl m.p.: 134-137°      C.;       254 CHCH.sub.3 O CH.sub.3  CN 2-Ethoxy-prop-2-yl IR (film): 2982,1717,13       36,1255,1210,1192,1067,1037,1010       255 CHCH.sub.3 O CH.sub.3  CN 2-i-Propoxy-prop-2-yl IR (film): 2983,1718      ,1383,1370,1255,1173,1119,1109,1037,1002       256 CHCH.sub.3 O CH.sub.3  CN 2-n-Butoxy-prop-2-yl IR (film): 2957,1718,      13 35,1255,1176,1036,1010,759       257 CHCH.sub.3 O CH.sub.3  CN 2-1-Butoxy-prop-2-yl IR (film): 2956,1717,      13 35,1366,1255,1209,1176,1064,1037,1008       258 CHCH.sub.3 O CH.sub.3  CN Cyclopropyl .sup.1 H-NMR (CDCl.sub.3):      δ =       0.9m, 1.6d, 2.3m, 3.67s, 5.15s, 7.05-7.4m                       259      CHCH.sub.3 O CH.sub.3  CN 2-Ethylthio-prop-2-yl .sup.1       H-NMR (CDCl.sub.3): δ = 1.1t, 1.5s, 1.6d, 2.2q, 3.7s, 5.1s,      7.1-7.5m       260 CHCH.sub.3 O CH.sub.3  CN 2-1-Propylthio-pro-2-yl .sup.1 H-NMR      (CDCl.sub.3): δ = 1.15s, 1.5s, 1.6d, 2.6m, 3.7s, 5.1s, 7.1-7.5m          261 CHCH.sub.3 O CH.sub.3  CN 2-Tetrahydropyranyl .sup.1 H-NMR      (CDCl.sub.3): δ =       1.4-1.9m, 1.6d, 3.5m, 3.7s, 4.1m, 5.1s, 7.0-7.5m

                                      TABLE IV                                     __________________________________________________________________________      ##STR29##                                                                     No.                                                                               X      Y R.sup.1                                                                           R.sup.3                                                                           R.sup.4    Data                                              __________________________________________________________________________     1  CHOCH.sub.3                                                                           O CH.sub.3                                                                          CH.sub.3                                                                          Phenyl                                                       2  CHOCH.sub.3                                                                           O CH.sub.3                                                                          CH.sub.3                                                                          3-Bromophenyl                                                3  CHOCH.sub.3                                                                           O CH.sub.3                                                                          CH.sub.3                                                                          4-Phenoxyphenyl                                              4  CHOCH.sub.3                                                                           O CH.sub.3                                                                          CH.sub.3                                                                          4-Cyclohexylphenyl                                           5  NOCH.sub.3                                                                            O CH.sub.3                                                                          CH.sub.3                                                                          Phenyl                                                       6  NOCH.sub.3                                                                            O CH.sub.3                                                                          CH.sub.3                                                                          3-Bromophenyl                                                                             oil; IR (film): 1727,1436,1312,1240,1032          7  NOCH.sub.3                                                                            O CH.sub.3                                                                          CH.sub.3                                                                          4-Phenoxyphenyl                                                                           oil; IR (film): 1727,1489,1239,1031,683           8  NOCH.sub.3                                                                            O CH.sub.3                                                                          CH.sub.3                                                                          4-Cyclohexylphenyl                                                                        oil; IR (film): 2925,1728,1447,1239,1164,1077                                  ,1032                                             9  CHOCH.sub.3                                                                           O CH.sub.3                                                                          CN Iso-Propyl oil; IR (film): 2970,2220,1710,1127               10 CHOCH.sub.3                                                                           O CH.sub.3                                                                          CN 2-Methoxyprop-2-yl                                                                        oil; IR (film): 2980,2220,1710,1127               11 CHOCH.sub.3                                                                           O CH.sub.3                                                                          CN 2-Methylthloprop-2-yl                                                                     oil; IR (film): 2980,2220,1709,1127               12 CHOCH.sub.3                                                                           O CH.sub.3                                                                          CN 2-Tetrahydrofuranyl                                                                       oil; IR (film): 2945,2850,2220,1709,1127          13 CHOCH.sub.3                                                                           O CH.sub.3                                                                          CN Phenyl     oil; IR (film): 2940,2220,1709,1127,1030          __________________________________________________________________________

                                      TABLE V                                      __________________________________________________________________________      ##STR30##                                                                     No.                                                                               R.sup.3                                                                          R.sup.4           Data                                                    __________________________________________________________________________     1  H H                                                                         2  H Methoxymethyl                                                             3  H Ethoxymethyl                                                              4  H n-Propoxymethyl                                                           5  H iso-Propoxymethyl                                                         6  H tert.-Butoxymethyl                                                        7  H 2-Methoxyprop-2-yl                                                        8  H 2-Ethoxyprop-2-yl                                                         9  H 2-n-Propoxyprop-2-yl                                                      10 H 2-iso-Propoxyprop-2-yl                                                    11 H 2-tert.-Butoxyprop-2-yl                                                   12 H Methylthiomethyl                                                          13 H tert.-Butylthiomethyl                                                     14 H 2-Methylthioprop-2-yl                                                     15 H 2-iso-Propylthioprop-2-yl                                                 16 H 2-tert.-Butylthioprop-2-yl                                                17 H Methyl                                                                    18 H Ethyl                                                                     19 H n-Propyl                                                                  20 H iso-Propyl                                                                21 H n-Butyl                                                                   22 H iso-Butyl                                                                 23 H sec.-Butyl                                                                24 H tert.-Butyl                                                               25 H n-Hexyl                                                                   26 H n-Decyl                                                                   27 H Cyclopropyl                                                               28 H Cyclohexyl                                                                29 H Phenylthiomethyl                                                          30 H 2-Phenylthiomethyl                                                        31 H 2-(2'-Chlorophonylthio)prop-2-yl                                          32 H Ethynyl                                                                   33 H 1-Propynyl                                                                34 H Methoxy                                                                   35 H Ethoxy                                                                    36 H n-Propoxy                                                                 37 H iso-Propoxy                                                               38 H n-Butoxy                                                                  39 H iso-Butoxy                                                                40 H sec.-Butoxy                                                               41 H tert.-Butoxy                                                              42 H Methylthio                                                                43 H Ethylthio                                                                 44 H n-Propylthio                                                              45 H iso-Propylthio                                                            46 H n-Butylthio                                                               47 H iso-Butylthio                                                             48 H sec.-Butylthio                                                            49 H tert.-Butylthio                                                           50 H Benzylthio                                                                51 H Trifluoromethoxy                                                          52 H Cyano                                                                     53 H Amino                                                                     54 H Methylamino                                                               55 H Dimethylamino                                                             56 H Ethylamino                                                                57 H Diethylamino                                                              58 H Di-n-Propylamino                                                          59 H Di-iso-Propylamino                                                        60 H Di-n-Butylamino                                                           61 H Di-iso-Butylamino                                                         62 H Acetyl                                                                    63 H Propion-1-yl                                                              64 H Butyr-1-yl                                                                65 H iso-Butyr-1-yl                                                            66 H Pivaloyl                                                                  67 H Benzoyl                                                                   68 H 4-Chlorobenzoyl                                                           69 H Benzylcarbonyl                                                            70 H Methoxycarbonyl                                                           71 H Ethoxycarbonyl                                                            72 H n-Propoxycarbonyl                                                         73 H iso-Propoxycarbonyl                                                       74 H n-Butoxycarbonyl                                                          75 H iso-Butoxycarbonyl                                                        76 H sec.-Butoxycarbonyl                                                       77 H tert.-Butoxycarbonyl                                                      78 H n-Hexoxycarbonyl                                                          79 H Phenoxycarbonyl                                                           80 H 4-Chlorphenoxycarbonyl                                                    81 H Benzyloxycarbonyl                                                         82 H Aminocarbonyl                                                             83 H Dimethylaminocarbonyl                                                     84 H Diethylaminocarbonyl                                                      85 H Di-iso-Propylaminocarbonyl                                                86 H Phenylaminocarbonyl                                                       87 H N-Methyl-N-Phenylaminocarbonyl                                            88 H Phenyl                                                                    89 H 2-Fluorophenyl    m.p.: 69-71° C.;                                 90 H 3-Fluorophenyl    m.p.: 74-77° C.;                                 91 H 4-Fluorophenyl    m.p.: 73-76° C.; IR (KBr): 1699,                                        1278,1271,1256,1225                                     92 H Pentafluarophenyl m.p.: 94-96° C.; IR (KBr): 1704,                                        1527,1494,1133                                          93 H 2-Chlorophenyl    .sup.1 H-NMR(CDCl.sub.3 3): δ = 3.70s,                                   3.82s, 5.15s, 7.15-7.40m,                                                      7.52m, 7.60s, 7.85m, 8.52s                              94 H 3-Chlorophenyl    m.p.: 48-50° C.;                                 95 H 4-Chlorophenyl    (v. Exaample 6)                                         96 H Pentachlorophenyl                                                         97 H 2,3-Dichlorophenyl                                                                               m.p.: 103-105° C.;                               98 H 2,4-Dtchlorophenyl                                                                               m.p.: 94-96° C.;                                 99 H 2,5-Dichlorophenyl                                                        100                                                                               H 2,6-Dichlorophenyl                                                                               m.p.: 118-120° C.;                               101                                                                               H 3,4-Dichlorophenyl                                                                               m.p.: 82-84° C.;                                 102                                                                               H 3,5-Dichlorophenyl                                                                               m.p.: 94-96° C.;                                 103                                                                               H 2,3,4-Trichlorophenyl                                                     104                                                                               H 2,3,5-Trichlorophenyl                                                     105                                                                               H 2,3,6-Trichlorophenyl                                                     106                                                                               H 2,4,5-Trichlorophenyl                                                     107                                                                               H 2,4,6-Trichlorophenyl                                                     108                                                                               H 3,4,5-Trichlorophenyl                                                     109                                                                               H 2,3,4,6-Tetrachlorophenyl                                                 110                                                                               H 2,3,5,6-Tetrachlorophenyl                                                 111                                                                               H 2-Bromophenyl     m.p.: 85-87° C.;                                 112                                                                               H 3-Bromophenyl     .sup.1 H-NMR (CDCl.sub.3): δ = 3.68s,                                    3.79s, 5.13, 7.15-7.54m, 7.59s                                                 7.74s, 8.00s                                            113                                                                               H 4-Bromophenyl     m.p.: 131-134° C.;                               114                                                                               H 2,4-Dibromophenyl                                                         115                                                                               H 3-Brom-4-fluorophenyl                                                     116                                                                               H 3-Brom-4-methoxyphenyl                                                    117                                                                               H 2-Iodophenyl                                                              118                                                                               H 3-Iodophenyl                                                              119                                                                               H 4-Iodophenyl                                                              120                                                                               H 2-Chloro-4-fluorophenyl                                                                          m.p.: 112-115° C.;                               121                                                                               H 2-Chloro-5-fluorophenyl                                                   122                                                                               H 2-Chloro-6-fluorophenyl                                                                          m.p.: 80-82° C.;                                 123                                                                               H 2-Chloro-4-bromophenyl                                                    124                                                                               H 2-Bromo-4-chlorophenyl                                                    125                                                                               H 2-Bromo-4-fluorophenyl                                                    126                                                                               H 3-Bromo-4-chlorophenyl                                                    127                                                                               H 3-Chloro-4-fluorophenyl                                                   128                                                                               H 3-Fluoro-4-chlorophenyl                                                   129                                                                               H 2-Cyanophenyl                                                             130                                                                               H 3-Cyanophenyl                                                             131                                                                               H 4-Cyanophenyl                                                             132                                                                               H 2-Nitrophenyl                                                             133                                                                               H 3-Nitrophenyl                                                             134                                                                               H 4-Nitrophenyl     m.p.: 147-155° C.;                               135                                                                               H 2-methylphenyl    m.p.: 57-59° C.;                                 136                                                                               H 3-Methylphenyl    m.p.: 54-56° C.;                                 137                                                                               H 4-Methylphenyl    m.p.: 86-88° C.;                                 138                                                                               H 2,4-Dimethylphenyl                                                                               m.p.: 75-77° C.;                                 139                                                                               H 2,6-Dimethylphenyl                                                        140                                                                               H 3,4-Dimethylphenyl                                                        141                                                                               H 3,5-Dimethylphenyl                                                        142                                                                               H 2,3,4-Trimethylphenyl                                                     143                                                                               H 2,3,5-Trimethylphenyl                                                     144                                                                               H 2,3,6-Trimethylphenyl                                                     145                                                                               H 2,4,5-Trimethylphenyl                                                     146                                                                               H 2,4,6-Trimethylphenyl                                                     147                                                                               H 3,4,5-Trimethylphenyl                                                     148                                                                               H Pentamethylphenyl                                                         149                                                                               H 2-Ethylphenyl                                                             150                                                                               H 3-Ethylphenyl                                                             151                                                                               H 4-Ethylphenyl                                                             152                                                                               H 3,5-Diethylphenyl                                                         153                                                                               H 2-n-Propylphenyl                                                          154                                                                               H 3-n-Propylphenyl                                                          155                                                                               H 4-n-Propylphenyl                                                          156                                                                               H 2-iso-propylphenyl                                                        157                                                                               H 3-iso-Propylphenyl                                                        158                                                                               H 4-iso-Propylphenyl                                                        159                                                                               H 2,4-Di-iso-Propylphenyl                                                   160                                                                               H 3,5-Di-iso-Propylphenyl                                                   161                                                                               H 4-n-Butylphenyl                                                           162                                                                               H 4-sec.-Butylphenyl                                                        163                                                                               H 4-iso-Butylphenyl                                                         164                                                                               H 4-tert.-Butylphenyl                                                                              m.p.: 71-73° C.                                  165                                                                               H 3-tert.-Butylphenyl                                                       166                                                                               H 2-tert.-Butylphenyl                                                       167                                                                               H 2,4-Di-tert.-Butylphenyl                                                  168                                                                               H 3,5-Di-tert.-Butylphenyl                                                  169                                                                               H 4-n-Hexylphenyl                                                           170                                                                               H 4-n-Dodecylphenyl                                                         171                                                                               H 2-Methyl-4-tert.-Butylphenyl                                              172                                                                               H 2-Methyl-6-tert.-outylphenyl                                              173                                                                               H 2-Methyl-4-iso-Propylphenyl                                               174                                                                               H 2-Methy1-4-cyclohexylphenyl                                               175                                                                               H 2-Methyl-4-phenylphenyl                                                   176                                                                               H 2-Methyl-4-benzylphenyl                                                   177                                                                               H 2-Methyl-4-phenoxyphenyl                                                  178                                                                               H 2-Methyl-4-benzyloxyphenyl                                                179                                                                               H 2-Methyl-3-chlorophenyl                                                   180                                                                               H 2-Methyl-4-chlorophenyl                                                   181                                                                               H 2-Methyl-5-chlorophenyl                                                   182                                                                               H 2-Methyl-6-chlorophenyl                                                   183                                                                               H 2-Methyl-4-fluorophenyl                                                   184                                                                               H 2-Methyl-3-bromophenyl                                                    185                                                                               H 2-Methyl-4-bromophenyl                                                    186                                                                               H 2-Methyl-3-methoxyphenyl                                                  187                                                                               H 2-Methyl-4-methoxyphenyl                                                  188                                                                               H 2-Methyl-5-methoxyphenyl                                                  189                                                                               H 2-Methyl-6-methoxyphenyl                                                  190                                                                               H 2-Methyl-4-iso-Propoxyphenyl                                              191                                                                               H 2-Methyl-2,5-dimethoxyphenyl                                              192                                                                               H 2-Methoxyphenyl   m.p.: 52-54° C.                                  193                                                                               H 3-Methoxyphenyl   .sup.1 H-NMR (CDCl.sub.3): δ = 3.65s,                                    3.76s, 3.80s, 5.12s,                                                           6.88-7.54m, 7.58s, 8.05s                                194                                                                               H 4-Methoxyphenyl   m.p.: 61-63° C.                                  195                                                                               H 2,3-Dimethoxyphenyl                                                       196                                                                               H 2,4-Dimethoxyphenyl                                                                              m.p.: 70-72° C.                                  197                                                                               H 2,5-Dimethoxyphenyl                                                       198                                                                               H 2,6-Dimethoxyphenyl                                                       199                                                                               H 3,4-Dimethoxyphenyl                                                       200                                                                               H 3,5-Dimethoxyphenyl                                                                              m.p.: 79-82° C.                                  201                                                                               H 3,6-Dimethoxyphenyl                                                       202                                                                               H 2,3,4-Trimethoxyphenyl                                                    203                                                                               H 2,3,5-Trimethoxyphenyl                                                    204                                                                               H 2,3,6-Trimethoxyphenyl                                                    205                                                                               H 2,4,5-Trimethoxyphenyl                                                    206                                                                               H 2,4,6-Trimethoxyphenyl                                                    207                                                                               H 3,4,5-Trimethoxyphenyl                                                    208                                                                               H 2-Ethoxyphenyl                                                            209                                                                               H 3-Ethoxyphenyl    .sup.1 H-NMR (CDCl.sub.3): δ = 1.39t,                                    3.67s, 3.80s, 4.02q, 5.12s,                                                    6.87-7.54m, 7.58s, 8.05s                                210                                                                               H 4-Ethoxyphenyl    m.p.: 93-94° C.                                  211                                                                               H 2-iso-Propoxyphenyl                                                       212                                                                               H 3-iso-Propoxyphenyl                                                       213                                                                               H 4-iso-Propoxyphenyl                                                       214                                                                               H 3-tert.-Butoxyphenyl                                                      215                                                                               H 4-tert.-Butoxyphenyl                                                                             .sup.1 H-NMR (CDCl.sub.3): δ = 1.36s,                                    3.68s, 3.78s, 5.09s,                                                           6.94-7.53m, 7.58s, 8.07s                                216                                                                               H 2-Trifluoromethoxyphenyl                                                  217                                                                               H 3-Trifluoromethoxyphenyl                                                  218                                                                               H 4-Trtfluorowthoxyphenyl                                                   219                                                                               H 3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                                   220                                                                               H 4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                                   221                                                                               H 2-Chloromethylphenyl                                                      222                                                                               H 3-Chloromethylphenyl                                                      223                                                                               H 4-Chloromethylphenyl                                                      224                                                                               H 2-Trifluoromethylphenyl                                                                          m.p.: 75-77° C.                                  225                                                                               H 3-Trifluoromethylphenyl                                                   226                                                                               H 4-Trifluoromethylphenyl                                                                          m.p.: 111-114° C.                                227                                                                               H 2-(Methoxyiminomethyl)phenyl                                              228                                                                               H 3-(Methoxyiminomethyl)phenyl                                              229                                                                               H 4-(Methoxyiminomethyl)phenyl                                              230                                                                               H 2-(Ethoxyiminomethyl)phenyl                                               231                                                                               H 3-(Ethoxyininomethyl)phenyl                                               232                                                                               H 4-(Ethoxyiminomthyl)phenyl                                                233                                                                               H 2-(n-Propoxyiminomethyl)phenyl                                            234                                                                               H 3-(n-Propoxyiminomethyl)phenyl                                            235                                                                               H 4-(n-Propoxyiminomethyl)phenyl                                            236                                                                               H 2-(iso-Propoxyiminomethyl)phenyl                                          237                                                                               H 3-(iso-Propoxyiminomethyl)phenyl                                          238                                                                               H 4-(iso-Propoxyiminomethyl)phenyl                                          239                                                                               H 2-(n-Butoxyiminomethyl)phenyl                                             240                                                                               H 3-(n-Butoxyiminomethyl)phenyl                                             241                                                                               H 4-(n-Butoxyiminomethyl)phenyl                                             242                                                                               H 2-(iso-Butoxyiminomethyl)phenyl                                           243                                                                               H 3-(iso-Butoxytminomethyl)phenyl                                           244                                                                               H 4-(iso-Butoxyiminomethyl)phenyl                                           245                                                                               H Z-(tert.-Butoxyiminamethyl)phenyl                                         246                                                                               H 3-(tert.-Butoxyiminomethyl)phenyl                                         247                                                                               H 4-(tert.-Butoxyiminomethyl)phenyl                                         248                                                                               H 2-(n-Pentoxyiminomethyl)phenyl                                            249                                                                               H 3-(n-Pentoxyiminomethyl)phenyl                                            250                                                                               H 4-(n-Pentoxyiminomethyl)phenyl                                            251                                                                               H 2-(n-Hexoxyiminomethyl)phenyl                                             252                                                                               H 3-(n-Hexoxyiminomethyl)phenyl                                             253                                                                               H 4-(n-Hexoxyiminomethyl)phenyl                                             254                                                                               H 2-(Allyloxyiminomethyl)phenyl                                             255                                                                               H 3-(Allyloxyiminomethyl)phenyl                                             256                                                                               H 4-(Allyloxyiminomethyl)phenyl                                             257                                                                               H 2-(Benzyloxyiminomethyl)phenyl                                            258                                                                               H 3-(Benzyloxyiminomethyl)phenyl                                            259                                                                               H 4-(Benzyloxyiminamethyl)phenyl                                            260                                                                               H 2-(Methoxyimino-1'-ethyl)phenyl                                           261                                                                               H 3-(Methoxyimino-1'-ethyl)phenyl                                           262                                                                               H 4-(Methoxytmino-1'-ethyl)phenyl                                           263                                                                               H 2-(Ethoxyimino-1'-ethyl)phenyl                                            264                                                                               H 3-(Ethoxyimino-1'-ethyl)phenyl                                            265                                                                               H 4-(Ethoxyimino-1'-ethyl)phenyl                                            266                                                                               H 2-(n-Propoxyimino-1'-ethyl)phenyl                                         267                                                                               H 3-(n-Propoxyimino-1'-ethyl)phenyl                                         268                                                                               H 4-(n-Propoxyimino-1'-ethyl)phenyl                                         269                                                                               H 2-(n-Butoxyamino-1'-ethyl)phenyl                                          270                                                                               H 3-(n-Butoxyanino-1'-ethyl)phenyl                                          271                                                                               H 4-(n-Butoxyamino-1'-ethyl)phenyl                                          272                                                                               H 2-(n-Pentoxyimino-1'-ethyl)phenyl                                         273                                                                               H 3-(n-Pentoxyimino-1'-ethyl)phenyl                                         274                                                                               H 4-(n-Pentoxyimino-1'-ethyl)phenyl                                         275                                                                               H 2-(n-Hexoxyimino-1'-ethyl)phenyl                                          276                                                                               H 3-(n-Hexoxyimino-1'-ethyl)phenyl                                          277                                                                               H 4-(n-Hexoxyimino-1'-ethyl)phenyl                                          278                                                                               H 2-(Allyloxyimino-1'-ethyl)phenyl                                          279                                                                               H 3-(Allyloxyimino-1'-ethyl)phenyl                                          280                                                                               H 4-(Allyloxyimino-1'-ethyl)phenyl                                          281                                                                               H 2-(Benzyloxyimino-1'-ethyl)phenyl                                         282                                                                               H 3-(Benzyloxyimino-1'-ethyl)phenyl                                         283                                                                               H 4-(Benzyloxyimino-1'-ethyl)phenyl                                         284                                                                               H 2-Phenylphenyl                                                            285                                                                               H 3-Phenylphenyl                                                            286                                                                               H 4-Phenylphenyl    m.p.: 94-96° C.                                  287                                                                               H 2-Phenoxyphenyl                                                           288                                                                               H 3-Phenoxyphenyl                                                           289                                                                               H 4-Phenoxyphenyl                                                           290                                                                               H 2-Benzyloxyphenyl                                                         291                                                                               H 3-Benzyloxyphenyl                                                         292                                                                               H 4-Benzyloxyphenyl m.p.: 94-96° C.                                  293                                                                               H 4-(Imidazol-1'-yl)phenyl                                                  294                                                                               H 4-(Piperazin-1'-yl)phenyl                                                 295                                                                               H 4-(Morpholin-1'-yl)phenyl                                                 296                                                                               H 4-(Piperidin-1'-yl)phenyl                                                 297                                                                               H 4-(Pyridyl-2'-oxy)phenyl                                                  298                                                                               H 2-Cyclopropylphenyl                                                       299                                                                               H 3-Cyclopropylphenyl                                                       300                                                                               H 4-Cyclopropylphenyl                                                       301                                                                               H 3-Cyclohexylphenyl                                                        302                                                                               H 4-Cyclohexylphenyl                                                        303                                                                               H 4-Oxiranylphenyl                                                          304                                                                               H 4-(1',3'-Dioxan-2'-yl)phenyl                                              305                                                                               H 4-(Tetrahydropyran-2-yloxy)phenyl                                         306                                                                               H 1-Naphthyl                                                                307                                                                               H 2-Naphthyl        oil; IR (film): 1707,                                                          1633,1257,1129,110                                      308                                                                               H 9-Anthryl                                                                 309                                                                               H 1-Naphtoxy                                                                310                                                                               H 2-Naphtoxy                                                                311                                                                               H 9-Anthroxy                                                                312                                                                               H Phenoxy                                                                   313                                                                               H 2-Chlorophenoxy                                                           314                                                                               H 3-Chlorophenoxy                                                           315                                                                               H 4-Chlorophenoxy                                                           316                                                                               H 4-Methylphenoxy                                                           317                                                                               H 4-tert.-Butylphenoxy                                                      318                                                                               H 4-Methoxyphenoxy                                                          319                                                                               H 4-Ethoxyphenoxy                                                           320                                                                               H 4-tert.-Butoxyphenoxy                                                     321                                                                               H Phenylthio                                                                322                                                                               H 2-Chlorophenylthio                                                        323                                                                               H 4-Chlorophenylthio                                                        324                                                                               H Benzyl                                                                    325                                                                               H 2-Methylbenzyl                                                            326                                                                               H 3-Methylbenzyl                                                            327                                                                               H 4-Methylbenyzl                                                            328                                                                               H 4-tert.-Butylbenzyl                                                       329                                                                               H 2-Chlorobenzyl                                                            330                                                                               H 3-Chlorobenzyl                                                            331                                                                               H 4-Chlorobenzyl                                                            332                                                                               H 2,4-Dichlorobenzyl                                                        333                                                                               H 2,6-Dichlorobenzyl                                                        334                                                                               H 2,4,6-Trichlorobenzyl                                                     335                                                                               H 2-Trifluoromethylbenzyl                                                   336                                                                               H 3-Trtfluaromethylbenzyl                                                   337                                                                               H 4-Trifluoromethylbenzyl                                                   338                                                                               H 2-Methoxybenzyl                                                           339                                                                               H 4-Methoxybenzyl                                                           340                                                                               H 4-tert.-Butoxybenzyl                                                      341                                                                               H 4-Phenoxybenzyl                                                           342                                                                               H 1-Phenethyl                                                               343                                                                               H 2-Phenethyl                                                               344                                                                               H 1-Phenylpropyl                                                            345                                                                               H 2-Phenylpropyl                                                            346                                                                               H 3-Phenylpropyl                                                            347                                                                               H 2-Methyl-2-phenylpropyl                                                   348                                                                               H 2-Methyl-3-phenylpropyl                                                   349                                                                               H 4-Phenylbutyl                                                             350                                                                               H 2-Phenyl-1-ethenyl                                                        351                                                                               H 1-Phenyl-1-ethenyl                                                        352                                                                               H 1-Phenyl-1-propenyl                                                       353                                                                               H 1-Phenyl-1-propen-2-yl                                                    354                                                                               H 2,2-Diphenylethenyl                                                       355                                                                               H Phenoxymethyl                                                             356                                                                               H 2-Pyridyl                                                                 357                                                                               H 3-Pyridyl                                                                 358                                                                               H 4-Pyridyl                                                                 359                                                                               H 2,6-Pyrimidinyl                                                           360                                                                               H 1,5-Pyrimidinyl                                                           361                                                                               H 2-Thienyl                                                                 362                                                                               H 3-Thienyl                                                                 363                                                                               H 2-Furyl                                                                   364                                                                               H 3-Furyl                                                                   365                                                                               H 1-Pyrrolyl                                                                366                                                                               H 1-Imidazolyl                                                              367                                                                               H 1,2,4-Triazolyl                                                           368                                                                               H 1,3,4-Triazolyl                                                           369                                                                               H 4-Thiazolyl                                                               370                                                                               H 2-Senzothiozolyl                                                          371                                                                               H 2-Pyridyloxy                                                              372                                                                               H 2-Pyrimidinyloxy                                                          373                                                                               H 2-Pyridylthio                                                             374                                                                               H 2-Pyrimidinylthio                                                         375                                                                               H 2-Benzothiozolylthio                                                      376                                                                               H Phenylthiomethyl                                                          377                                                                               H 2-Pyridylmethyl                                                           378                                                                               H 3-Pyridylmethyl                                                           379                                                                               H Furfuryloxy                                                               380                                                                               H Thienylmthoxy                                                             381                                                                               H 3-Isoxazolylmethoxy                                                       382                                                                               4 2-Oxazolylmethoxy                                                         383                                                                               4 2-Pyridylmethoxy                                                          384                                                                               H 2'-Furyl-2-ethenyl                                                        385                                                                               H 2'-Thienyl-2-ethenyl                                                      386                                                                               H 3'-Pyridyl-2-ethenyl                                                      387                                                                               H Oxiranyl                                                                  388                                                                               H 1-Aziridinyl                                                              389                                                                               H 1-Azetidinyl                                                              390                                                                               H 1-Pyrrolidinyl                                                            391                                                                               H 2-Tetrahydrofuryl                                                         392                                                                               H 2-Tetrahydropyranyl                                                       393                                                                               H 3-Tetrahydropyranyl                                                       394                                                                               H 1-Piperidinyl                                                             395                                                                               H 1-Morpholinyl                                                             396                                                                               H i-Piperazinyl                                                             397                                                                               H 1,3-Dioxan-2-yl                                                           398                                                                               H 3-Tetrahydrothiopyranyl                                                   399                                                                               H 2-Dihydropyranyloxy                                                       400                                                                               H 2-Tetrahydropyranyloxy                                                    401                                                                               H CF.sub.3                                                                  402                                                                               H 2-Fluoroethyl                                                             403                                                                               H 2,2,2-Trifluoroethyl                                                      404                                                                               m Pentafluoroethyl                                                          405                                                                               H Chloromethyl                                                              406                                                                               H Dichloromethyl                                                            407                                                                               H Trichloromethyl                                                           408                                                                               H 2-Chloroethyl                                                             409                                                                               H 2,2,2-Trichloroethyl                                                      410                                                                               H Pentachloroothyl                                                          411                                                                               H Cyclopropyl                                                               412                                                                               H Cyclobutyl                                                                413                                                                               H cyclopentyl                                                               414                                                                               H Cyclohexyl                                                                415                                                                               H 1-Methylcyclopropyl                                                       416                                                                               H 2,2-Dimethylcyclopropyl                                                   417                                                                               H 1-Methylcyclohexyl                                                        418                                                                               H 2,2-Difluorocyclopropyl                                                   419                                                                               H 2,2-Dichloracyclopropyl                                                   420                                                                               H 2,2-Dibromocyclopropyl                                                    421                                                                               H 2,2-Dichloro-3-Methylcyclopropyl                                          422                                                                               H 2,2,3,3-Tetrafluorocyclobutyl                                             423                                                                               H Ethenyl                                                                   424                                                                               H 1-Propenyl                                                                425                                                                               H 2-Methyl-1-propenyl                                                       426                                                                               H 4-Methylpent-3-en-1-yl                                                    427                                                                               H 2-Propenyl                                                                428                                                                               H 2-Butenyl                                                                 429                                                                               H 1-Methyl-2-propenyl                                                       430                                                                               H 3-Methyl-2-butenyl                                                        431                                                                               H 2,2-Difluoroethenyl                                                       432                                                                               H 2,2-Dichloroethenyl                                                       433                                                                               H 3,3,3-Trifluoropropenyl                                                   434                                                                               H 3,3,3-Trichloropropenyl                                                   435                                                                               H 3-Chloro-2-propenyl                                                       436                                                                               H Cyclopent-1-enyl                                                          437                                                                               H Cyclopentadienyl                                                          438                                                                               H Cyclohex-1-enyl                                                           439                                                                               H Pentafluorocyclopentadienyl                                               440                                                                               H Pentachlorocyclopentadienyl                                               441                                                                               H 4-Dimethylaminaphenyl                                                                            m.p.: 90-92° C.                                  442                                                                               H 4-n-Butoxyphenyl  m.p.: 79-82° C.                                  __________________________________________________________________________

                                      TABLE VI                                     __________________________________________________________________________      ##STR31##                                                                     No.                                                                               R.sup.3                                                                          R.sup.4           Data                                                    __________________________________________________________________________     1  H H                 m.p.: 94-95° C.                                  2  H Methoxymethyl                                                             3  H Ethoxymethyl                                                              4  H n-Propoxymethyl                                                           5  H iso-Propoxymethyl                                                         6  H tert.-Butoxymethyl                                                        7  H 2-Methoxyprop-2-yl                                                        8  H 2-Ethoxyprop-2-yl                                                         9  H 2-n-Propoxyprop-2-yl                                                      10 H 2-iso-Propoxyprop-2-yl                                                    11 H 2-tert.-Butoxyprop-2-yl                                                   12 H Methylthiomethyl                                                          13 H tert.-Butylthiomethyl                                                     14 H 2-methylthioprop-2-yl                                                     15 H 2-iso-Propylthioprop-2-yl                                                 16 H 2-tert.-Butylthioprop-2-yl                                                17 H Methyl                                                                    18 H Ethyl                                                                     19 H n-Propyl                                                                  20 H iso-Propyl                                                                21 H n-Butyl                                                                   22 H iso-Butyl                                                                 23 H sec.-Butyl                                                                24 H tert.-Butyl                                                               25 H n-Hexyl                                                                   26 H n-Decyl                                                                   27 H Cyclopropyl                                                               28 H Cyclohexyl                                                                29 H Phenylthiomethyl                                                          30 H 2-Phenylthiomethyl                                                        31 H 2-(2'-Chlorophenylthio)prop-2-yl                                          32 H Ethynyl                                                                   33 H 1-Propynyl                                                                34 H Methoxy                                                                   35 H Ethoxy                                                                    36 H n-Propoxy                                                                 37 H iso-Propoxy                                                               38 H n-Butoxy                                                                  39 H iso-Butoxy                                                                40 H sec.-Butoxy                                                               41 H tert.-Butoxy                                                              42 H Methylthio                                                                43 H Ethylthio                                                                 44 H n-Propylthio                                                              45 H iso-Propylthio                                                            46 H n-Butylthio                                                               47 H iso-Butylthio                                                             48 H sec.-Butylthio                                                            49 H tert.-Butylthio                                                           50 H Benzylthio                                                                51 H Trifluoromethoxy                                                          52 H Cyano                                                                     53 H Amino                                                                     54 H Methylamino                                                               55 H Dimethylamino                                                             56 H Ethylamino                                                                57 H Diethylamino                                                              58 H Di-n-Propylanino                                                          59 H Di-iso-Propylamino                                                        60 H Di-n-Butylamino                                                           61 H Di-iso-Butylamino                                                         62 H Acetyl                                                                    63 H Propion-1-yl                                                              64 H Butyr-1-yl                                                                65 H iso-Butyr-1-yl                                                            66 H Pivaloyl                                                                  67 H Benzoyl                                                                   68 H 4-Chlorobenzoyl                                                           69 H Benzylcarbonyl                                                            70 H Methoxycarbonyl                                                           71 H Ethoxycarbonyl                                                            72 H n-Propoxycarbonyl                                                         73 H iso-Propoxycarbonyl                                                       74 H n-Butoxycarbonyl                                                          75 H iso-Butoxycarbonyl                                                        76 H sec.-Butoxycarbonyl                                                       77 H tert.-Butoxycarbonyl                                                      78 H n-Hexoxycarbonyl                                                          79 H Phenoxycarbonyl                                                           80 H 4-Chlorophenoxycarbonyl                                                   81 H Benzyloxycarbonyl                                                         82 H Aminocarbonyl                                                             83 H Dimethylaminocarbonyl                                                     84 H Diethylaminocarbonyl                                                      85 H Di-iso-Propylaminocarbonyl                                                86 H Phenylaminocarbonyl                                                       87 H N-Methyl-N-Phenylaminocarbonyl                                            88 H Phenyl            m.p.: 92-95° C.                                  89 H 2-Fluorophenyl    m.p.: 92-95° C.                                  90 H 3-Fluorophenyl    m.p.: 58-60° C.                                  91 H 4-Fluorophenyl    m.p.: 110-111° C.                                92 H Pentafluorophenyl m.p.: 118-120° C.                                93 H 2-Chlorophenyl    .sup.1 H-NMR(CDCl.sub.3): δ = 3.70s,                                     3.82s, 5.15s, 7.15-7.40m,                                                      7.52m, 7.60s, 7.85m, 8.52s                              94 H 3-Chlorophenyl    m.p.: 58-60° C.                                  95 H 4-Chlorophenyl    m.p.: 146-148° C.                                96 H Pentachlorophenyl                                                         97 H 2,3-Dichlorophenyl                                                                               m.p.: 95-97° C.                                  98 H 2,4-Dichlorophenyl                                                                               m.p.: 58-62° C.                                  99 H 2,5-Dichlorophenyl                                                        100                                                                               H 2,6-Dichlorophenyl                                                                               m.p.: 136-140° C.                                101                                                                               H 3,4-Dichlorophenyl                                                                               m.p.: 94-97° C.                                  102                                                                               N 3,5-Dichlorophenyl                                                                               m.p.: 88-91° C.                                  103                                                                               H 2,3,4-Trichlorophenyl                                                     104                                                                               N 2,3,5-Trichlorophenyl                                                     105                                                                               H 2,3,6-Trichlorophenyl                                                     106                                                                               H 2,4,5-Trichlorophenyl                                                     107                                                                               H 2,4,6-Trichlorophenyl                                                     108                                                                               H 3,4,5-Trichlorophenyl                                                     109                                                                               H 2,3,4,6-Tetrachlorophenyl                                                 110                                                                               H 2,3,5,6-Tetrachlorophenyl                                                 111                                                                               H 2-Bromophenyl     m.p.: 91-94° C.                                  112                                                                               H 3-Bromophenyl     m.p.: 63-64° C.                                  113                                                                               H 4-Bromophenyl     m.p.: 145-147° C.                                114                                                                               H 2,4-Dibromophenyl                                                         115                                                                               H 3-Bromo-4-Fluorophenyl                                                    116                                                                               H 3-Bromo-4-Methoxyphenyl                                                   117                                                                               H 2-Iodophenyl                                                              118                                                                               H 3-Iodophenyl                                                              119                                                                               H 4-Iodophenyl                                                              120                                                                               H 2-Chloro-4-Fluorophenyl                                                                          m.p.: 90-93° C.                                  121                                                                               H 2-Chloro-5-Fluorophenyl                                                   122                                                                               H 2-Chloro-6-Fluorophenyl                                                                          m.p.: 111-113° C.                                123                                                                               H 2-Chloro-4-Bromophenyl                                                    124                                                                               H 2-Bromo-4-Chlorophenyl                                                    125                                                                               H 2-Bromo-4-Fluorophenyl                                                    126                                                                               H 3-Bromo-4-Chlorophenyl                                                    127                                                                               H 3-Chloro-4-Fluorophenyl                                                   128                                                                               H 3-Fluoro-4-Chlorophenyl                                                   129                                                                               H 2-Cyanophenyl                                                             130                                                                               H 3-Cyanophenyl                                                             131                                                                               H 4-Cyanophenyl                                                             132                                                                               H 2-Nitrophenyl                                                             133                                                                               H 3-Nitrophenyl                                                             134                                                                               H 4-Nitrophenyl     m.p.: 142-146° C.                                135                                                                               H 2-Methylphenyl    m.p.: 58-60° C.                                  136                                                                               H 3-Methylphonyl    m.p.: 70-72° C.                                  137                                                                               H 4-Methylphenyl    m.p.: 99-102° C.                                 138                                                                               H 2,4-Dimethylphenyl                                                                               m.p.: 54-56° C.                                  139                                                                               H 2,6-Dimethylphenyl                                                        140                                                                               H 3,4-Dimethylphenyl                                                        141                                                                               H 3,5-Dimethylphenyl                                                        142                                                                               H 2,3,4-Trimethylphenyl                                                     143                                                                               H 2,3,5-Trimethylphenyl                                                     144                                                                               H 2,3,6-Trimethylphenyl                                                     145                                                                               H 2,4,5-Trimethylphenyl                                                     146                                                                               H 2,4,6-Trimethylphenyl                                                     147                                                                               H 3,4,5-Trimethylphenyl                                                     148                                                                               H Pentamethylphenyl                                                         149                                                                               H 2-Ethylphenyl                                                             150                                                                               H 3-Ethylphenyl                                                             151                                                                               H 4-Ethylphenyl                                                             152                                                                               H 3,5-Diethylphonyl                                                         153                                                                               H 2-n-Propylphenyl                                                          154                                                                               H 3-n-Propylphenyl                                                          155                                                                               H 4-n-Propylphenyl                                                          156                                                                               H 2-iso-Propylphenyl                                                        157                                                                               H 3-iso-Propylphenyl                                                        158                                                                               H 4-iso-Propylphenyl                                                        159                                                                               H 2,4-Di-iso-Propylphenyl                                                   160                                                                               H 3,5-Di-iso-Propylphenyl                                                   161                                                                               H 4-n-Butylphenyl                                                           162                                                                               H 4-sec.-Butylphenyl                                                        163                                                                               H 4-iso-Butylphenyl                                                         164                                                                               H 4-tert.-Butylphenyl                                                                              m.p.: 82-84° C.                                  165                                                                               H 3-tert.-Butylphenyl                                                       166                                                                               H 2-tert.-Butylphenyl                                                       167                                                                               H 2,4-Di-tert.-Butylphenyl                                                  168                                                                               H 3,5-Di-tert.-Butylphenyl                                                  169                                                                               H 4-n-Hexylphenyl                                                           170                                                                               H 4-n-Dodecylphenyl                                                         171                                                                               H 2-Methyl-4-tert.-Butylphenyl                                              172                                                                               H 2-Methyl-6-tert.-Butylphenyl                                              173                                                                               H 2-Methyl-4-iso-Propylphenyl                                               174                                                                               H 2-Methyl-4-Cyclohexylphenyl                                               175                                                                               H 2-Methyl-4-Phenylphenyl                                                   176                                                                               H 2-Methyl-4-Benzylphenyl                                                   177                                                                               H 2-Methyl-4-Phenoxyphenyl                                                  178                                                                               H 2-Methyl-4-Benzyloxyphenyl                                                179                                                                               H 2-Methyl-3-Chlorophenyl                                                   180                                                                               H 2-Methyl-4-Chlorophenyl                                                   181                                                                               H 2-Methyl-5-Chlorophenyl                                                   182                                                                               H 2-Methyl-6-Chlorophenyl                                                   183                                                                               H 2-Methyl-4-Fluorophenyl                                                   184                                                                               H 2-Methyl-3-Bromophenyl                                                    185                                                                               H 2-Methyl-4-Bromophenyl                                                    186                                                                               H 2-Methyl-3-Methoxyphenyl                                                  187                                                                               H 2-Methyl-4-Methoxyphenyl                                                  188                                                                               H 2-Methyl-5-Methoxyphenyl                                                  189                                                                               H 2-Methyl-6-Methoxyphenyl                                                  190                                                                               H 2-Methyl-4-iso-Propoxyphenyl                                              191                                                                               H 2-Methyl-2,5-Dimethoxyphenyl                                              192                                                                               H 2-Methoxyphenyl   m.p.: 65-68° C.                                  193                                                                               H 3-Methoxyphenyl   m.p.: 83-84° C.                                  194                                                                               H 4-Methoxyphenyl   m.p.: 88-90° C.                                  195                                                                               H 2,3-Dimethoxyphenyl                                                       196                                                                               H 2,4-Dimethoxyphenyl                                                                              m.p.: 90-93° C.                                  197                                                                               H 2,5-Dimethoxyphenyl                                                       198                                                                               H 2,6-Dimethoxyphenyl                                                       199                                                                               H 3,4-Dimethoxyphenyl                                                                              m.p.: 70-72° C.                                  200                                                                               H 3,5-Dimethoxyphenyl                                                                              m.p.: 97-99° C.                                  201                                                                               H 3,6-Dimethoxyphenyl                                                       202                                                                               H 2,3,4-Trimethoxyphenyl                                                    203                                                                               H 2,3,5-Trimethoxyphemyl                                                    204                                                                               H 2,3,6-Trimethoxyphenyl                                                    205                                                                               H 2,4,5-Trimethoxyphenyl                                                    206                                                                               H 2,4,6-Trimethoxyphenyl                                                    207                                                                               H 3,4,5-Trimethoxyphenyl                                                                           m.p.: 105-109° C.                                208                                                                               H 2-Ethoxyphenyl                                                            209                                                                               H 3-Ethoxyphenyl    m.p.: 90-92° C.                                  210                                                                               H 4-Ethoxyphenyl    m.p.: 97-98° C.                                  211                                                                               H 2-iso-Propoxyphenyl                                                       212                                                                               H 3-iso-Propoxyphenyl                                                       213                                                                               H 4-iso-Propoxyphenyl                                                       214                                                                               H 3-tert.-Butoxyphenyl                                                      215                                                                               H 4-tert.-Butoxyphenyl                                                                             m.p.: 78-83° C.                                  216                                                                               H 2-Trifluoromethoxyphenyl                                                  217                                                                               H 3-Trifluoromethoxyphenyl                                                  218                                                                               H 4-Trifluoromethoxyphenyl                                                  219                                                                               H 3-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                                   220                                                                               H 4-(1',1',2',2'-Tetrafluoro)ethoxyphenyl                                   221                                                                               H 2-Chloromethylphenyl                                                      222                                                                               H 3-Chloromethylphenyl                                                      223                                                                               H 4-Chloromethylphenyl                                                      224                                                                               H 2-Trifluoromethylphenyl                                                                          m.p.: 58-60° C.                                  225                                                                               H 3-Trifluoromethylphenyl                                                                          m.p.: 74-77° C.                                  226                                                                               H 4-Trifluoromethylphenyl                                                                          m.p.: 120-122° C.                                227                                                                               H 2-(Methoxyiminomethyl)phenyl                                              228                                                                               H 3-(Methoxyiminomethyl)phenyl                                              229                                                                               H 4-(Methoxyiminomethyl)phenyl                                              230                                                                               H 2-(Ethoxyiminomethyl)phenyl                                               231                                                                               H 3-(Ethoxyiminomethyl)phenyl                                               232                                                                               H 4-(Ethoxyiminomethyl)phenyl                                               233                                                                               H 2-(n-Propoxyiminomethyl)phenyl                                            234                                                                               H 3-(n-Propoxyiminomethyl)phenyl                                            235                                                                               H 4-(n-Propoxyiminomethyl)phenyl                                            236                                                                               H 2-(iso-Propoxyiminomethyl)phenyl                                          237                                                                               H 3-(iso-Propoxyiminomethyl)phenyl                                          238                                                                               H 4-(iso-Propoxyiminomethyl)phenyl                                          239                                                                               H 2-(n-Butoxyiminomethyl)phenyl                                             240                                                                               H 3-(n-Butoxyiminomethyl)phenyl                                             241                                                                               H 4-(n-Butoxyiminomethyl)phenyl                                             242                                                                               H 2-(iso-Butoxyiminomethyl)phenyl                                           243                                                                               H 3-(iso-Butoxyiminomethyl)phenyl                                           244                                                                               H 4-(iso-Butoxyiminomethyl)phenyl                                           245                                                                               H 2-(tert.-Butoxyiminomethyl)phenyl                                         246                                                                               H 3-(tert.-Butoxyiminomethyl)phenyl                                         247                                                                               H 4-(tert.-Butoxyiminomethyl)phonyl                                         248                                                                               H 2-(n-Pentoxyiminomethyl)phenyl                                            249                                                                               H 3-(n-Pentoxyininomethyl)phenyl                                            250                                                                               H 4-(n-PentoxyiminoMethyl)phenyl                                            251                                                                               H 2-(n-Hexoxyiminomethyl)phenyl                                             252                                                                               H 3-(n-Hexoxyiminomethyl)phenyl                                             253                                                                               H 4-(n-Hexoxyiminomethyl)phenyl                                             254                                                                               H 2-(Allyloxyiminomethyl)phenyl                                             255                                                                               H 3-(Allyloxyiminomethyl)phenyl                                             256                                                                               H 4-(Allyloxyiminomethyl)phenyl                                             257                                                                               H 2-(Benzyloxytainomethyl)phenyl                                            258                                                                               H 3-(Benzyloxyininomethyl)phenyl                                            259                                                                               H 4-(Benzyloxyiminomethyl)phenyl                                            260                                                                               H 2-(Methoxyimino-1'-ethyl)phenyl                                           261                                                                               H 3-(Methoxyimino-1'-ethyl)phenyl                                           262                                                                               H 4-(Methoxyimino-1'-ethyl)phenyl                                           263                                                                               H 2-(Ethoxyimino-1'-ethyl)phenyl                                            264                                                                               H 3-(Ethoxyimino-1'-ethyl)phenyl                                            265                                                                               H 4-(Ethoxyimino-1'-ethyl)phenyl                                            266                                                                               H 2-(n-Propoxyimino-1'-ethyl)phenyl                                         267                                                                               H 3-(n-Propoxyimino-1'-ethyl)phenyl                                         268                                                                               H 4-(n-Propoxyimino-1'-ethyl)phenyl                                         269                                                                               H 2-(n-Butoxyamino-1'-ethyl)phenyl                                          270                                                                               H 3-(n-Butoxyanino-1'-ethyl)phenyl                                          271                                                                               H 4-(n-Butoxyamino-1'-ethyl)phenyl                                          272                                                                               H 2-(n-Pentoxyimino-1'-ethyl)phenyl                                         273                                                                               H 3-(n-Pentoxyimino-1'-ethyl)phenyl                                         274                                                                               H 4-(n-Pentoxyimino-1'-ethyl)phenyl                                         275                                                                               H 2-(n-Hexoxyimino-1'-ethyl)phenyl                                          276                                                                               H 3-(n-Hexoxyimino-1'-ethyl)phenyl                                          277                                                                               H 4-(n-Hexoxyimino-1'-ethyl)phenyl                                          278                                                                               H 2-(Allyloxyimino-1'-ethyl)phenyl                                          279                                                                               H 3-(Allyloxyimino-1'-ethyl)phenyl                                          280                                                                               H 4-(Allyloxyimino-1'-ethyl)phenyl                                          281                                                                               H 2-(Benzyloxyimino-1'-ethyl)phenyl                                         282                                                                               H 3-(Benzyloxyimino-1'-ethyl)phenyl                                         283                                                                               H 4-(Benzyloxyimino-1'-ethyl)phenyl                                         284                                                                               H 2-Phenylphenyl                                                            285                                                                               H 3-Phenylphenyl                                                            286                                                                               H 4-Phenylphenyl    m.p.: 100-102° C.                                287                                                                               H 2-Phenoxyphenyl                                                           288                                                                               H 3-Phenoxyphenyl   IR (film): 1728,1489,                                                          1247,1214,1070,1020                                     289                                                                               H 4-Phenoxyphenyl   m.p.: 85-87° C.                                  290                                                                               H 2-Benzyloxyphenyl m.p.: 83-85° C.                                  291                                                                               H 3-Benzyloxyphenyl m.p.: 66-68° C.                                  292                                                                               H 4-Benzyloxyphenyl m.p.: 104-106° C.                                293                                                                               H 4-(Imidazol-1'-yl)phenyl                                                  294                                                                               H 4-(Piperazin-1'-yl)phenyl                                                 295                                                                               H 4-(Morpholin-1'-yl)phenyl                                                 296                                                                               H 4-(Piperidin-1'-yl)phenyl                                                 297                                                                               H 4-(Pyridyl-2'-oxy)phenyl                                                  298                                                                               H 2-Cyclopropylphenyl                                                       299                                                                               H 3-Cyclopropylphenyl                                                       300                                                                               H 4-Cyclopropylphenyl                                                       301                                                                               H 3-Cyclohexylphenyl                                                        302                                                                               H 4-Cyclohexylphenyl                                                        303                                                                               H 4-Oxiranylphenyl                                                          304                                                                               H 4-(1',3'-Dioxan-2'-yl)phenyl                                              305                                                                               H 4-(Tetrahydropyran-2-yloxy)phenyl                                         306                                                                               H 1-Naphthyl        m.p.: 70-73° C.                                  307                                                                               H 2-Naphthyl        m.p.: 125-126° C.                                308                                                                               H 9-Anthryl                                                                 309                                                                               H 1-Naphthoxy                                                               310                                                                               H 2-Naphthoxy                                                               311                                                                               H 9-Anthroxy                                                                312                                                                               H Phenoxy                                                                   313                                                                               H 2-Chlorophenoxy                                                           314                                                                               H 3-Chlorophenoxy                                                           315                                                                               H 4-Chlorophenoxy                                                           316                                                                               H 4-Methylphenoxy                                                           317                                                                               H 4-tert.-Butylphenoxy                                                      318                                                                               H 4-Methoxyphenoxy                                                          319                                                                               H 4-Ethoxyphenoxy                                                           320                                                                               H 4-tert.-Butoxyphenoxy                                                     321                                                                               H Phenylthio                                                                322                                                                               H 2-Chlorophenylthio                                                        323                                                                               H 4-Chlorophenylthio                                                        324                                                                               H Benzyl                                                                    325                                                                               H 2-Methylbenzyl                                                            326                                                                               H 3-Methylbenzyl                                                            327                                                                               H 4-Methylbenyzl                                                            328                                                                               H 4-tert.-Butylbenzyl                                                       329                                                                               H 2-Chlorobenzyl                                                            330                                                                               H 3-Chlorobenzyl                                                            331                                                                               H 4-Chlorobenzyl                                                            332                                                                               H 2,4-Dichlorobenzyl                                                        333                                                                               H 2,6-Dichlorobenzyl                                                        334                                                                               H 2,4,6-Trichlorobenzyl                                                     335                                                                               H 2-Trifluoromethylbenzyl                                                   336                                                                               H 3-Trifluoromethylbenzyl                                                   337                                                                               H 4-Trifluoromethylbenzyl                                                   338                                                                               H 2-Methoxybenzyl                                                           339                                                                               H 4-Methoxybenzyl                                                           340                                                                               H 4-tert.-Butoxybenzyl                                                      341                                                                               H 4-Phenoxybenzyl                                                           342                                                                               H 1-Phenethyl                                                               343                                                                               H 2-Phenethyl                                                               344                                                                               H 1-Phenylpropyl                                                            345                                                                               H 2-Phenylpropyl                                                            346                                                                               H 3-Phenylpropyl                                                            347                                                                               H 2-Methyl-2-phenylpropyl                                                   348                                                                               H 2-Methyl-3-phenylpropyl                                                   349                                                                               H 4-Phenylbutyl                                                             350                                                                               H 2-Phenyl-1-ethenyl                                                        351                                                                               H 1-Phenyl-1-ethenyl                                                        352                                                                               H 1-Phenyl-1-propenyl                                                       353                                                                               H 1-Phenyl-1-propen-2-yl                                                    354                                                                               H 2,2-Diphenylethenyl                                                       355                                                                               H Phenoxymethyl                                                             356                                                                               H 2-Pyridyl                                                                 357                                                                               H 3-Pyridyl                                                                 358                                                                               H 4-Pyridyl                                                                 359                                                                               H 2,6-Pyrimidinyl                                                           360                                                                               H 1,5-Pyrimidinyl                                                           361                                                                               H 2-Thienyl                                                                 362                                                                               H 3-Thienyl                                                                 363                                                                               H 2-Furyl                                                                   364                                                                               H 3-Furyl                                                                   365                                                                               H 1-Pyrrolyl                                                                366                                                                               H 1-Imidazolyl                                                              367                                                                               H 1,2,4-Triazolyl                                                           368                                                                               H 1,3,4-Triazolyl                                                           369                                                                               H 4-Thiazolyl                                                               370                                                                               H 2-Benzothiazolyl                                                          371                                                                               H 2-Pyridyloxy                                                              372                                                                               H 2-Pyrimidinyloxy                                                          373                                                                               H 2-Pyridylthio                                                             374                                                                               H 2-Pyrimidinylthio                                                         375                                                                               H 2-Benzothiazolylthio                                                      376                                                                               H Phenylthiomethyl                                                          377                                                                               H 2-Pyridylmethyl                                                           378                                                                               H 3-Pyridylmethyl                                                           379                                                                               H Furfuryloxy                                                               380                                                                               H Thienylmethoxy                                                            381                                                                               H 3-Isoxazolylmethoxy                                                       382                                                                               H 2-Oxazolylmethoxy                                                         383                                                                               H 2-Pyridylmethoxy                                                          384                                                                               H 2'-Furyl-2-ethenyl                                                        385                                                                               H 2'-Thienyl-2-ethenyl                                                      386                                                                               H 3'-Pyridyl-2-ethenyl                                                      387                                                                               H Oxiranyl                                                                  388                                                                               H 1-Aziridinyl                                                              389                                                                               H 1-Azetidinyl                                                              390                                                                               H I-Pyrrolidinyl                                                            391                                                                               H 2-Tetrahydrofuryl                                                         392                                                                               H 2-Tetrahydropyranyl                                                       393                                                                               H 3-Tetrahydropyranyl                                                       394                                                                               H 1-Piperidinyl                                                             395                                                                               H 1-Morpholinyl                                                             396                                                                               H 1-Piperazinyl                                                             397                                                                               H 1,3-Dioxan-2-yl                                                           398                                                                               H 3-Tetrahydrothiopyranyl                                                   399                                                                               H 2-Dihydropyranyloxy                                                       400                                                                               H 2-Tetrahydropyranyloxy                                                    401                                                                               H CF.sub.3                                                                  402                                                                               H 2-Fluoroethyl                                                             403                                                                               H 2,2,2-Trifluoroethyl                                                      404                                                                               H Pentafluoroethyl                                                          405                                                                               H Chloromethyl                                                              406                                                                               H Dichloromethyl                                                            407                                                                               H Trichloromethyl                                                           408                                                                               H 2-Chloroethyl                                                             409                                                                               H 2,2,2-Trichloroethyl                                                      410                                                                               H Pentachloroethyl                                                          411                                                                               H Cyclopropyl                                                               412                                                                               H Cyclobutyl                                                                413                                                                               H Cyclopentyl                                                               414                                                                               H Cyclohexyl                                                                415                                                                               H 1-Methylcyclopropyl                                                       416                                                                               H 2,2-Dimethylcyclopropyl                                                   417                                                                               H 1-Methylcyclohexyl                                                        418                                                                               H 2,2-Difluorocyclopropyl                                                   419                                                                               H 2,2-Dichlorocyclopropyl                                                   420                                                                               H 2,2-Dibromocyclopropyl                                                    421                                                                               H 2,2-Dichloro-3-methylcyclopropyl                                          422                                                                               H 2,2,3,3-Tetrafluorocyclobutyl                                             423                                                                               H Ethenyl                                                                   424                                                                               H 1-Propenyl                                                                425                                                                               H 2-Methyl-1-propenyl                                                       426                                                                               H 4-Methylpent-3-en-1-yl                                                    427                                                                               H 2-Propenyl                                                                428                                                                               H 2-Butenyl                                                                 429                                                                               H 1-Methyl-2-propenyl                                                       430                                                                               H 3-Methyl-2-butenyl                                                        431                                                                               H 2,2-Difluoroethenyl                                                       432                                                                               H 2,2-Dichloroethenyl                                                       433                                                                               H 3,3,3-Trifluoropropenyl                                                   434                                                                               H 3,3,3-Trichloropropenyl                                                   435                                                                               H 3-Chloro-2-propenyl                                                       436                                                                               H Cyclopent-1-enyl                                                          437                                                                               H Cyclopentadienyl                                                          438                                                                               H Cyclohex-1-enyl                                                           439                                                                               H Pentafluorocyclopentadienyl                                               440                                                                               H Pentachlorocyclopentadienyl                                               441                                                                               H 4-Dimethylaminophenyl                                                                            m.p.: 70-71° C.                                  442                                                                               H 4-Allyloxyphenyl  m.p.: 81-83° C.                                  443                                                                               H Diphenylmethyl    m.p.: 66-68° C.                                  444                                                                               H Dimethylbenzyl    .sup.1 H-NMR (CDCl.sub.3): δ = 1.45s                                     3.78s, 4.03s, 5.00s                                                            7.17-7.41m                                              __________________________________________________________________________

                  TABLE VII                                                        ______________________________________                                          ##STR32##                                                                     No.       R.sub.n.sup.8   Data                                                 ______________________________________                                         1         H               m.p. 156-158° C.                              2         3-Fluoro                                                             3         4-Fluoro                                                             4         3-Chloro                                                             5         4-Chloro                                                             6         3-Bromo                                                              7         4-Bromo                                                              8         3-Iodo                                                               9         4-Iodo                                                               10        3,4-Dichloro                                                         11        3,5-Dichloro                                                         12        3,6-Dichloro                                                         13        4,5-Dichloro                                                         14        3,4,5-Trichloro                                                      15        3,4,6-Trichloro                                                      16        3,4,5,6-Tetrachloro                                                  17        3,4,5,6-Tetrafluoro                                                  18        3,4,5,6-Tetrabromo                                                   19        3,5-Difluoro                                                         20        3,5-Dibromo                                                          21        3-Methyl                                                             22        4-Methyl                                                             23        3-Ethyl                                                              24        4-Ethyl                                                              25        3-iso-Propyl                                                         26        4-iso-Propyl                                                         27        3-tert-Butyl                                                         28        4-tert-Butyl                                                         29        3,4-Dimethyl                                                         30        3,5-Dimethyl                                                         31        3,6-Dimethyl                                                         32        4,5-Dimethyl                                                         33        3,4,5-Trimthyl                                                       34        3,4,6-Trimethyl                                                      35        3,4,5,6-Tetramethyl                                                  36        3-Nitro                                                              37        4-Nitro                                                              38        3,5-Dinitro                                                          39        3-Cyano                                                              40        4-Cyano                                                              41        3-Methoxy                                                            42        4-Methoxy                                                            43        3-tert.Butoxy                                                        44        4-tert.Butoxy                                                        45        3-Trifluoromethyl                                                    46        4-Trifluoromethyl                                                    47        3-Chloromethyl                                                       48        4-Chloromethyl                                                       49        3-Trifluoromethoxy                                                   50        4-Trifluoromethoxy                                                   51        3-Benzyloxy                                                          52        4-Benzyloxy                                                          53        4,5-Dibenzyloxy                                                      54        3-Phenoxy                                                            55        4-Phenoxy                                                            56        3-Phenyl                                                             57        4-Phenyl                                                             58        3-Pyrid-2'-yl                                                        59        4-Pyrid-2'-yl                                                        60        3-Pyrid-2'-yloxy                                                     61        4-Pyrid-2'-yloxy                                                     ______________________________________                                    

                  TABLE VIII                                                       ______________________________________                                          ##STR33##                                                                     No.       R.sup.8 n       Data                                                 ______________________________________                                         1         H               m.p. 152-155° C.                              2         3-Fluoro                                                             3         4-Fluoro                                                             4         3-Chloro                                                             5         4-Chloro                                                             6         3-Bromo                                                              7         4-Bromo                                                              8         3-Iodo                                                               9         4-Iodo                                                               10        3,4-Dichloro                                                         11        3,5-Dichloro                                                         12        3,6-Dichloro                                                         13        4,5-Dichloro                                                         14        3,4,5-Trichloro                                                      15        3,4,6-Trichloro                                                      16        3,4,5,6-Tetrachloro                                                  17        3,4,5,6-Tetrafluoro                                                  18        3,4,5,6-Tetrabromo                                                   19        3,5-Difluoro                                                         20        3,5-Dibromo                                                          21        3-Methyl                                                             22        4-Methyl                                                             23        3-Ethyl                                                              24        4-Ethyl                                                              25        3-iso-Propyl                                                         26        4-iso-Propyl                                                         27        3-tert-Butyl                                                         28        4-tert-Butyl                                                         29        3,4-Dimethyl                                                         30        3,5-Dimethyl                                                         31        3,6-Dimethyl                                                         32        4,5-Dimethyl                                                         33        3,4,5-Trimethyl                                                      34        3,4,6-Trimethyl                                                      35        3,4,5,6-Tetramethyl                                                  36        3-Nitro                                                              37        4-Nitro                                                              38        3,5-Dinitro                                                          39        3-Cyano                                                              40        4-Cyano                                                              41        3-Methoxy                                                            42        4-Methoxy                                                            43        3-tert.Butoxy                                                        44        4-tert.Butoxy                                                        45        3-Trifluoromethyl                                                    46        4-Trifluoromethyl                                                    47        3-Chloromethyl                                                       48        4-Chloromethyl                                                       49        3-Trifluoromethoxy                                                   50        4-Trifluoromethoxy                                                   51        3-Benzyloxy                                                          52        4-Benzyloxy                                                          53        4,5-Dibenzyloxy                                                      54        3-Phenoxy                                                            55        4-Phenoxy                                                            56        3-Phenyl                                                             57        4-Phenyl                                                             58        3-Pyrid-2'-yl                                                        59        4-Pyrid-2'-yl                                                        60        3-Pyrid-2'-yloxy                                                     61        4-Pyrid-2'-yloxy                                                     ______________________________________                                    

                  TABLE IX                                                         ______________________________________                                          ##STR34##                                                                     No.   X           Y       R.sup.1                                                                              R.sup.8  Data                                  ______________________________________                                         1     CHSCH.sub.3 O       CH.sub.3                                                                             H                                              2     CHSCH.sub.3 NH      CH.sub.3                                                                             H                                              3     CHSCH.sub.3 S       CH.sub.3                                                                             H                                              4     CH.sub.2    O       CH.sub.3                                                                             N                                              5     CH.sub.2    NH      CH.sub.3                                                                             H                                              6     CH.sub.2    S       CH.sub.3                                                                             H                                              7     CHCH.sub.3  O       CH.sub.3                                                                             H                                              8     CHCH.sub.3  NH      CH.sub.3                                                                             H                                              9     CHCH.sub.3  S       CH.sub.3                                                                             H                                              10    CHCH.sub.3  O       CH.sub.3                                                                             Perchloro                                      11    CHCH.sub.3  NH      CH.sub.3                                                                             Perchloro                                      12    CHCH.sub.3  S       CH.sub.3                                                                             Perchloro                                      13    CHOCH.sub.3 NH      CH.sub.3                                                                             H                                              14    CHOCH.sub.3 S       CH.sub.3                                                                             H                                              15    CHOCH.sub.3 NH      CH.sub.3                                                                             Perchloro                                      16    CHOCH.sub.3 S       CH.sub.3                                                                             Perchloro                                      17    NOCH.sub.3  NH      CH.sub.3                                                                             H                                              18    NOCH.sub.3  S       CH.sub.3                                                                             H                                              19    NOCH.sub.3  NH      CH.sub.3                                                                             Perchloro                                      20    NOCH.sub.3  S       CH.sub.3                                                                             Perchloro                                      ______________________________________                                    

In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in curcurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi themselves, or the plants, seed or materials to be protected against fungus attack, or the soil are treated with a fungicidally effective amount of the active ingredient.

The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as ligninsulfite waste liquors and methylcellulose.

The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, e.g., on Paecilomyces variotii. When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally required.

The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 429 (Table I) and 10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for application in the form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 14 (Table II), 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 49 (Table I), 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finally dispersing the solution in water, an aqueous dispersion is obtained.

IV. An aqueous dispersion of 20 parts by weight of compound no. 56 (Table I), 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely distributing the solution in water, an aqueous dispersion is obtained.

V. A hammer-milled mixture of 80 parts by weight of compound no. 14 (Table I), 3 parts by weight of the sodium salt of diisobutylnaphthalene α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.

VI. An intimate mixture of 3 parts by weight of compound no. 17 (Table II) and 97 parts by weight of particulate kaolin. The dust contains 3 wt % of the active ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 17 (Table I), 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 571 (Table I), 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts by weight of water, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 616 (Table I), 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.

USE EXAMPLES

The active ingredient used for comparison purposes was 2-(phenoxymethyl) phenylglyoxylic acid-methyl ester-O-methyloxime (A) disclosed in EP 253,213.

Use Example 1

Action on wheat brown rust

Leaves of pot-grown wheat seedlings of the "Kanzler" variety were dusted with spores of brown rust (Puccinia recondita). The pots were then placed for 24 hours at 20° to 22° C. in a high-humidity (90-95%) chamber. During this period the spores germinated and the germ tubes penetrated the leaf tissue. The infected plants were then sprayed to runoff with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were set up in the greenhouse at 20° to 22° C. and a relative humidity of 65 to 70%. The extent of rust fungus spread on the leaves was assessed after 8 days.

The results show that active ingredients nos. 49, 429, 56, 14, 15, 16, 17, 582, 578, 573, 592, 571, 704, 705 and 616 from Table I and nos. 17 and 644 from Table II, applied as 0.025 wt% spray liquors, have a better fungicidal action (95%) than prior art comparative compound A (50%).

Use Example 2

Action on Pyricularia oryzae (protective)

Leaves of pot-grown rice seedlings of the "Bahia" variety were sprayed to runoff with aqueous emulsions containing (dry basis) 80% of active ingredient and 20% of emulsifier, and inoculated 24 hours later with an aqueous spore suspension of Pyricularia oryzae. The plants were then set up in climatic cabinets at 22° to 24° C. and 95 to 99% relative humidity. The extent of fungus attack was assessed after 6 days.

The results show that active ingredients nos. 429, 583, 593, 592, 571, 706 and 616 from Table I and nos. 14, 15, 16, 17, 582, 592, 571, 769, 782, 672, 644 and 583 from Table II, applied as 0.05 wt % spray liquors, have a very good fungicidal action (100%).

The novel compounds are also suitable for effectively combating pests such as insects, arachnids and nematodes. They may be used as pesticides in crop protection and in the hygiene, stores protection and veterinary sector.

Examples of injurious insects belonging to the Lepidoptera order are Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Platypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis.

Examples from the Coleoptera order are Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotretra nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria.

Examples from the Diptera order are Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa. Examples from the Thysanoptera order are Franklinella fusca, Franklinielle occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci.

Examples from the Hymenoptera order are Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta.

Examples from the Heteroptera order are Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor.

Examples from the nematodes class are root-knot nematodes, e.g., Meloidogyne hapla, Meloidogyne incognita and Meloidogyne javanica, cyst-forming nematodes, e.g., Globodera rostochiensis, Heterodera avenae, Hetrodera glycinae, Heterodera schachtii and Heterodera trifolii, and stem and leaf eelworms, e.g., Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

When the active ingredients are used for combating pests, the concentrations in the finished formulations may vary over a wide range. Generally, the concentration is from 0.0001 to 10, and preferably from 0.001 to 0.1, %.

The active ingredients may also be successfully used in the ultra-low-volume method (ULV), where it is possible to apply formulations containing more than 95 wt % of active ingredient, or even the active ingredient without any additives.

When the active ingredients are used for combating pests in the open, the application rates are from 0.01 to 10, and preferably from 0.1 to 1.0, kg/ha.

Use Example 3

Tetranychus telarius (spider mite); contact action--spray test

Potted bush beans which had developed the first pair of true leaves and were heavily infested with all stages of the spider mite Tetranychus telarius were sprayed to runoff in a spray cabinet with aqueous formulations of the active ingredients. The plants were placed on a rotating disc and sprayed from all sides with 50 ml of spray liquor. The plants were heavily infested with mites and numerous eggs had been laid on them. The action was assessed after 5 days by means of a binocular microscope. During this period, the plants were kept under normal greenhouse conditions.

    ______________________________________                                                        Application rate                                                                            Mortality                                                         in ppm       In %                                               ______________________________________                                         Compound no.                                                                   from Table I                                                                   49             100          80                                                 36             100          80                                                 43             1000         100                                                429            1000         100                                                38             40           100                                                39             100          100                                                45             1000         100                                                582            about 20     100                                                579            20           80                                                 583            40           100                                                573            20           100                                                593            1000         80                                                 592            40           100                                                704            about 20     100                                                705            40           100                                                Compound no.                                                                   from Table II                                                                  37             1000         100                                                39             1000         100                                                45             1000         100                                                ______________________________________                                    

Use Example 4

Musca domestica (housefly); continuous contact action

Both the tops and bottoms of Petri dishes 10 cm in diameter were lined with a total of 1 ml of acetonic solutions of the active ingredients. After the solvent had evaporated (about 30 mins.) , 10 flies and absorbent cotton steeped in water were introduced into each dish and the dishes closed. The flies in supine position were counted after 24 hours.

If a kill rate of 80 to 100% occurs at a concentration of 0.01 mg/dish, the test is continued with falling concentrations.

    ______________________________________                                         Compound no.   Application rate                                                                           Mortality                                           from Table I   in mg       in %                                                ______________________________________                                         49             0.1         80                                                  36             1.0         80                                                  37             0.1         100                                                 582            0.1         80                                                  593            0.1         60                                                  705            0.1         100                                                 706            0.1         100                                                 ______________________________________                                    

Use Example 5

Plutella maculipennis (diamondback moth); ingestion-inhibiting action

Young kohlrabi leaves are dipped for 3 seconds into aqueous solutions of the candidate compounds, and then placed on a round filter paper 9 cm in diameter which has been moistened with 0.5 ml of water. The filter paper is then placed in a Petri dish 10 cm in diameter. 10 caterpillars in the 4th larval stage are then placed on each leaf, and the Petri dish is closed. Ingestion inhibition is determined in % after 48 hours.

    ______________________________________                                         Compound no.   Application rate                                                                           Mortality                                           from Table I   in ppm      in %                                                ______________________________________                                         49             200         80                                                  36             200         80                                                  429            1000        80                                                  16             400         80                                                  582            400         100                                                 593            1000        80                                                  592            400         80                                                  705            400         80                                                  706            400         80                                                  ______________________________________                                    

Use Example 6

Action on Peronospora in grapes

Leaves of potted vines of the "M uller Thurgau" variety were sprayed with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action of the active ingredients, the plants were, after the sprayed-on layer had dried, set up in the greenhouse for 8 days. Only then were the leaves infected with a zoospore suspension of Plasmopara viticola. The vines were then placed for 48 hours in a water-vapor-saturated chamber at 24° C. and then for 5 days in a greenhouse at from 20° to 30° C. To accelerate the sporangiophore discharge, the plants were then again set up in the moist chamber for 16 hours. The extent to which the leaves had been attacked was then assessed.

The results show that active ingredients nos. 49, 429, 56, 14, 15, 16, 17, 582, 578, 573, 592, 571, 704, 705, 616, 117, 156, 579, 583, 593 and 706 from Table I, Nos. 17, 644, 117, 429, 56, 43, 36, 49, 14, 15, 16, 582, 614 and 672 from Table II, and compound no. 1 from Table VII have, when applied as 0.025 wt % spray liquors, a better fungicidal action (95%) than the prior art comparative agent A (50%). 

We claim:
 1. An O-benzyloxime ether of the formula I ##STR35## wherein X is CH--C₁₋₄ alkylY is O, S or NR⁵ ; R¹, R² and R⁵ are H or C₁ -C₄ -alkyl; Z¹ and Z² are identical or different and each is H, halogen, methyl, methoxy or cyano; R³ is hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloakenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, C₁ -C₄ -alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C₁ -C₄ -alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁ -C₄ -alkyl, substituted or unsubstituted aryl-C₂ -C₄ -alkenyl, substituted or unsubstituted aryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted arylthio-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heteroaryl-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl-C₂ -C₄ -alkenyl, substituted or unsubstituted hetaryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted heterocyclyloxy, halogen, N(R⁶)₂, where the radical R⁶ are identical or different and each is H, C₁ -C₆ -alkyl or substituted or unsubstituted phenyl, --CO--N(R⁷)₂, where the radicals R⁷ are identical or different and each is H or C₁ -C₄ -alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, -C₃ -C₆ -cycloalkyl, heterocyclyl, heterocyclyloxy; and R⁴ is substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heteroaryl-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl-C₁ -C₄ -alkenyl, substituted or unsubstituted hetaryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted heterocyclyloxy.
 2. The O-benzyloxime ether of claim 1, of the formula (II) ##STR36##
 3. The O-benzyloxime ether of claim 1, of the formula (II) ##STR37##
 4. The O-benzyloxime ether of claim 1, wherein X is CHCH₃ or CHCH₂ CH₃.
 5. The O-benzyloxime ether of claim 1, wherein Z¹ and Z² are hydrogen.
 6. The O-benzyloxime ether of claim 1, wherein R¹ is methyl.
 7. The O-benzyloxime ether of claim 1, wherein R² is hydrogen.
 8. The O-benzyloxime ether of claim 1, wherein R³ is selected from the group consisting of cyano, methyl and ethyl.
 9. The O-benzyloxime ether of claim 1, wherein R⁴ is substituted hetaryl.
 10. The O-benzyloxime ether of claim 1, wherein R⁴ is substituted by a radical selected from the group consisting of halogen, phenyl, methyl, ethyl, iso-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl and 2,2,2-trifluoroethoxy.
 11. The O-benzyloxime ether of claim 1, wherein R⁴ is substituted pyridyl or pyrimidyl.
 12. The O-benzyloxime ether of claim 1, wherein R⁴ is substituted pyrimidyl, wherein the substitution is adjacent to a pyrimidyl-nitrogen.
 13. The O-benzyloxime ether of claim 1, wherein R⁴ is substituted by a radical selected from the group consisting of C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₂ haloalkyl, C₁₋₂ haloalkoxy, phenyl and substituted phenyl.
 14. A fungicide containing an inert carrier and a fungicidally effective amount of an O-benzyloxime ether of the formula I ##STR38## wherein X is CH--CH₁₋₄ ;Y is O, S or NR⁵ ; R¹, R² and R⁵ are H or C₁ -C₄ -alkyl; Z¹ and Z² are indentical or different and each is H, halogen, methyl, methoxy or cyano; R³ is hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, C₁ -C₄ -alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C₁ -C₄ -alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁ -C₄ -alkyl, substituted or unsubstituted aryl-C₂ -C₄ -alkenyl, substituted or unsubstituted aryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted arylthio-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heteroaryl-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl-C₂ -C₄ -alkenyl, substituted or unsubstituted hetaryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted heterocyclyloxy, halogen, N(R⁶)₂, where the radicals R⁶ are identical or different and each is H, C₁ -C₆ -alkyl or substituted or unsubstituted phenyl, --CO--N(R⁷)₂, where the radicals R⁷ are identical or different and each is H or C₁ -C₄ -alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, --C₃ -C₆ -cycloalkyl, heterocyclyl, heterocyclyloxy; and R⁴ is substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heteroaryl-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl-C₂ -C₄ -alkenyl, substituted or unsubstituted hetaryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted heterocyclyloxy.
 15. A process for combating fungi, wherein the fungi, or the materials, plants or seed threatened by fungus attack, or the soil, are treated with a fungicidally effective amount of a compound of the formula I ##STR39## wherein X is CH--CH₁₋₄ ;Y is 0, S or NR⁵ ; R¹, R² and R⁵ are H or C₁ -C₄ alkyl; Z¹ and Z² are identical or different and each is H, halogen, methyl, methoxy or cyano; R³ is hydrogen, cyano, straight-chain or branched C₁ -C₁₀ -alkyl, C₁ -C₄ -haloalkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -halocycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₁ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, arylthio-C₁ -C₄ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₅ -haloalkenyl, C₃ -C₆ -cycloalkenyl, C₃ -C₆ -halocycloalkenyl, C₂ -C₆ -alkynyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₄ -alkylthio, benzylthio, C₁ -C₄ -alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, C₁ -C₄ -alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted aryl-C₁ -C₄ -alkyl, substituted or unsubstituted aryl-C₂ -C₄ -alkenyl, substituted or unsubstituted aryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted arylthio-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heteroaryl-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl-C₂ -C₄ -alkenyl, substituted or unsubstituted hetaryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted heterocyclyloxy, halogen, N(R⁶)₂, where the radicals R⁶ are identical or different and each is H, C₁ -C₆ -alkyl or substituted or unsubstituted phenyl, --CO--N(R⁷)₂, where the radicals R⁷ are identical or different and each is H or C₁ -C₄ -alkyl, substituted or unsubstituted meaning, in addition to hydrogen, the radicals halogen, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, C₁ -C₁₀ -alkoximino-C₁ -C₂ -alkyl, aryl, aryloxy, benzyloxy, hetaryl, hetaryloxy, -C₃ -C₆ -cycloalky, heterocyclyl, heterocyclyloxy; and R⁴ is substituted or unsubstituted hetaryl, substituted or unsubstituted hetaryloxy, substituted or unsubstituted hetarylthio, substituted or unsubstituted heteroaryl-C₁ -C₄ -alkyl, substituted or unsubstituted hetaryl-C₂ -C₄ -alkenyl, substituted or unsubstituted hetaryloxy-C₁ -C₄ -alkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted heterocyclyloxy. 